multi-component reaction was reported for the synthesis of 7-ester indoles and bis-indoles under microwave-assisted conditions,enriching and expanding the library of heterocyclic compounds.This reaction started from e...multi-component reaction was reported for the synthesis of 7-ester indoles and bis-indoles under microwave-assisted conditions,enriching and expanding the library of heterocyclic compounds.This reaction started from enamine ketone,aromatic ketone aldehyde hydrate,and carboxylic acid,and selectively synthesized 7-ester indoles and bis-indoles by changing the substituted enamine ketone substrate.This method had the characteristics of high regional selectivity,short reaction time,and green environmental protection.展开更多
Skeletal editing has emerged as a powerful tool in organic chemistry,enabling the simplification of synthetic routes to complex molecules[1].Indoles,electron-rich nitrogen-containing building blocks,represent privileg...Skeletal editing has emerged as a powerful tool in organic chemistry,enabling the simplification of synthetic routes to complex molecules[1].Indoles,electron-rich nitrogen-containing building blocks,represent privileged scaffolds prevalent in pharmaceuticals,natural products,and bioactive compounds.The application of skeletal editing strategies to modify such structures is highly valuable and in growing demand.Leveraging the electronrich nature of indoles at C2 and C3,single-carbon atom insertion using cationic carbyne equivalents offers an efficient approach for indole ring expansion to quinoline(Scheme 1a).However,existing methods predominantly rely on halocarbene precursors,which restricts the functional groups of ring-expanded products to halogen[2],alkyl,aryl,heteroaryl and ester moieties[3].This limitation hinders their utility in late-stage skeletal modifications of complex targets.展开更多
Indoles and their derivatives are an important class of N-heterocycles.In this article,iridium-catalyzed annulation reactions of N-aryl-2-aminopyridines to synthesize indole derivatives are designed and developed,whic...Indoles and their derivatives are an important class of N-heterocycles.In this article,iridium-catalyzed annulation reactions of N-aryl-2-aminopyridines to synthesize indole derivatives are designed and developed,which utilize vinylene carbonate as a new C2 synthon.This protocol is expected to provide a facile and useful access to various indole derivatives.展开更多
Difluoromethyl compounds are widely found in natural products,bioactive molecule and pharmaceuticals.A visible-light induced difluoromethylation/cyclization of 2-aryl indoles is described to construct indolo[2,1-a]iso...Difluoromethyl compounds are widely found in natural products,bioactive molecule and pharmaceuticals.A visible-light induced difluoromethylation/cyclization of 2-aryl indoles is described to construct indolo[2,1-a]isoquinolin-6(5H)-one derivatives using the inexpensive and easy-to-handle HCF_(2)SO_(2)Na as an HCF2 sources.Diverse difluoromethylated indolo[2,1-a]isoquinolines were readily obtained in moderate to good yields.Mechanistic studies demonstrate that the reaction may involve a radical process.展开更多
Indole[2,1-α]isoquinolines are an important class of bioactive molecules and show good antibacterial activity.In the present study,an efficient copper(I)-catalyzed acylation/cyclization has been developed for the con...Indole[2,1-α]isoquinolines are an important class of bioactive molecules and show good antibacterial activity.In the present study,an efficient copper(I)-catalyzed acylation/cyclization has been developed for the construction of indolo[2,1-α]isoquinoline derivatives by utilizing 2-aryl-N-acryloyl indole and benzohydrazide as reactants in the presence of CuI as catalyst and tert-butyl hydroperoxide as oxidant.The present protocol exhibits good functional group tolerance,and a series of acylated indole[2,1-α]isoquinolines were synthesized in moderate to good yields.Radical trapping experiments indicated that the reaction may involve a radical process.展开更多
Cycloheptatriene is a privileged structural motif present in many bioactive compounds,pharmaceutical agents and natural products,especially in a large number of core structures of sesquiterpenoids.Herein,a mild and ef...Cycloheptatriene is a privileged structural motif present in many bioactive compounds,pharmaceutical agents and natural products,especially in a large number of core structures of sesquiterpenoids.Herein,a mild and efficient synthetic approach was reported for access of a series of C2 or C3-(cycloheptatrienyl)-substituted indoles.A wide range of functional groups can be well tolerated in this transformation,especially including hydroxyl,halo,carboxylic acid and its derivative groups.Based on these results,a rational mechanism via electrophilic substitution of indoles with tropylium tetrafluoroborate is proposed.展开更多
Recently,more and more bacteria have been reported to become tolerant to antibiotics.In this study,one tnaA gene involved in indole production,and the effect of exogenous indole on the formation of persister cells spe...Recently,more and more bacteria have been reported to become tolerant to antibiotics.In this study,one tnaA gene involved in indole production,and the effect of exogenous indole on the formation of persister cells specific to tetracycline in Vibrio splendidus were characterized.The tnaA Vs gene was first cloned and conditionally expressed in Escherichia coli Rosetta(DE3).To investigate the regulatory effect of TnaA Vs,the tnaA deletion strain AJ01/ΔtnaA was constructed by in-frame deletion.The undetected extracellular indole in the AJ01/ΔtnaA indicated that TnaA was the solo enzyme to produce indole in V.splendidus.The drop plate method showed that AJ01/ΔtnaA was more tolerant to the higher concentration of tetracycline than that of AJ01,being 340-fold higher in the proportion of survived cells when cell density OD 600≈0.65.Moreover,the synergistic effects of indole and tetracycline on killing of V.splendidus were determined.Results show that addition of 2-mmol/L indole increased the susceptibility of both AJ01 and AJ01/ΔtnaA to 10×minimum inhibitory concentration tetracycline.To explore the genes and pathways regulated by TnaA Vs,the transcriptomic analysis between AJ01 and AJ01/ΔtnaA was performed.Result shows that TCA cycle,arginine biosynthesis,quorum sensing and microbial metabolism in diverse environments were downregulated,while the ribosome pathways,the protein metabolic process,peptide biosynthetic and metabolic process were upregulated in the AJ01/ΔtnaA.This study shows that indole could enhance the bactericidal effect of tetracycline on V.splendidus by decreased ribosome level probably but increased ATP level.展开更多
BACKGROUND Indolent T-cell lymphoma of the gastrointestinal tract(iTCL-GI)is a rare mature T-cell lymphoma that has been formally recognized as a distinct entity in the 5th Edition World Health Organization Classifica...BACKGROUND Indolent T-cell lymphoma of the gastrointestinal tract(iTCL-GI)is a rare mature T-cell lymphoma that has been formally recognized as a distinct entity in the 5th Edition World Health Organization Classification of Tumours of Haematolymphoid Tumours.However,the coexistence of iTCL-GI with epithelial malignancies is rare in clinical practice.This study reports a case of iTCL-GI with gastric signet-ring cell carcinoma(SRCC).We aim to increase diagnostic awareness among clinicians and pathologists regarding multiple primary tumors.CASE SUMMARY A 65-year-old female presented with a 5-month history of lower abdominal pain,bloating,and vomiting.An abdominal computed tomography scan revealed irregular thickening of the gastric wall.Endoscopy revealed diffuse mucosal edema and rigid mucosa along the lesser curvature of the gastric body.There was a 1.5 cm mucosal protrusion on the greater curvature.Biopsy revealed that the lamina propria was expanded by a dense,nondestructive infiltrate of small lymphocytes in the greater curvature,which were characterized by a CD3+/CD8+/TIA-1+immunophenotype with a low Ki-67 index.Clonal T-cell receptor rearrangement was detected,but the Epstein-Barr virus encoded RNA's was negative.Lesions on the lesser curvature of the gastric body were confirmed to be SRCCs.After three months of follow-up,the patient completed four cycles of chemotherapy targeting the SRCC.While her abdominal pain improved,she experienced a weight loss of 5 kg.CONCLUSION Clinicians and pathologists must integrate assessment of these rare cases to prevent misdiagnosis and guide clinical practice.展开更多
BACKGROUND Indolent NK-cell lymphoproliferative disorder of the gastrointestinal tract(iNKLPD)is a rare and recently defined entity,recognized in the 2022 WHO classification of hematolymphoid tumors.iNKLPD typically e...BACKGROUND Indolent NK-cell lymphoproliferative disorder of the gastrointestinal tract(iNKLPD)is a rare and recently defined entity,recognized in the 2022 WHO classification of hematolymphoid tumors.iNKLPD typically exhibits a benign or slowly progressive clinical course,with disease localized to the gastrointestinal tract.Here,we present what we believe to be the first reported case of iNKLPD associated with protein-losing enteropathy(PLE),characterized by a poor response to chemotherapy and rapid clinical deterioration,culminating in death within a few months.CASE SUMMARY We report the case of a 64-year-old man who presented with bilateral lower-extremity edema and fatigue.Laboratory tests revealed marked hypoalbuminemia,while other liver function parameters remained within normal limits.Renal and cardiac function assessments were unremarkable.Histopathological examination of endoscopic biopsies confirmed a diagnosis of iNKLPD of the gastrointestinal tract.The patient was treated with oral prednisone and cyclosporine,which led to temporary improvement in both symptoms and serum albumin levels.However,disease relapse occurred during corticosteroid tapering,accompanied by worsening hypoalbu-minemia and refractory diarrhea.The patient died eight months after diagnosis,likely due to disease progression or severe treatment-related complications.CONCLUSION iNKLPD generally exhibits an indolent course;nonetheless,the prognosis may be poor if secondary PLE is involved.展开更多
An efficient protocol was developed for the synthesis of 3-aminoalkylated indoles using 3- chlorophenylboronic acid as a catalyst under ambient temperature conditions.The three-component reaction of indoles,aromatic a...An efficient protocol was developed for the synthesis of 3-aminoalkylated indoles using 3- chlorophenylboronic acid as a catalyst under ambient temperature conditions.The three-component reaction of indoles,aromatic aldehydes and N-methyl aniline offered corresponding 3-aminoalkylated indoles in excellent yields.This protocol presents some remarkable features such as mild reaction conditions,simple workup procedure and excellent yields.展开更多
Sulfamic acid was proved to be a cost-effective and recyclable catalyst for Friedel-Crafts type reaction of indole withα,β-unsaturated carbonyl compound and benzyl alcohol.Various indoles,α,β-unsaturated carbonyl ...Sulfamic acid was proved to be a cost-effective and recyclable catalyst for Friedel-Crafts type reaction of indole withα,β-unsaturated carbonyl compound and benzyl alcohol.Various indoles,α,β-unsaturated carbonyl compounds and a benzyl alcohol were successfully used in this type of reaction,and the corresponding products were obtained in good to excellent yields.展开更多
One new monoterpenoid indole alkaloid, l l-methoxyburnamine-17-O-3′,4′,5′-trimethoxybenzoate （1）, was isolated from Rauvolfia yunnanensis Tsiang. Its structure was identified by speclroscopic evidences.
This work presents a new greener alternative for biocondensation of aldehydes and indoles for the synthesis of bis- and tris(indolyl)methanes catalyzed by lemon juice (Citrus limon) in good yields under ultrasound irr...This work presents a new greener alternative for biocondensation of aldehydes and indoles for the synthesis of bis- and tris(indolyl)methanes catalyzed by lemon juice (Citrus limon) in good yields under ultrasound irradiation in aqueous ethanol. Various substituted aldehydes with indoles under this reaction condition are elucidated. Also, tetraindolyl compounds were prepared using terephthaldialdehyde by following the same protocol. This method is an environmentally benign, efficient reaction, which requires shorter reaction time and simple experimental and work-up procedures.展开更多
Herein,we reported a convenient and efficient multicomponent reaction of indoles,selenium powder and unactivated alkyl halides.This protocol provides a practical,and facile approach for the synthesis of 3-alkylselenin...Herein,we reported a convenient and efficient multicomponent reaction of indoles,selenium powder and unactivated alkyl halides.This protocol provides a practical,and facile approach for the synthesis of 3-alkylselenindole derivatives.The advantages of this strategy include mild and transition-metal-free conditions,broad functional group tolerance,the use of simple and easily accessible seleniium powder and alkyl halides as coupling partners.More importantly,the reaction proceeded smoothly with a large scale(>10 g,>90%yield),which further highlighted the potential application of this selenation strategy.展开更多
Trichloroacetyl) indole has been synthesized by the reaction of indole with trichloroacetyl chloride in 73% yield, and its crystal structure was determined by X-ray diffraction method. The crystal is of orthorhombic...Trichloroacetyl) indole has been synthesized by the reaction of indole with trichloroacetyl chloride in 73% yield, and its crystal structure was determined by X-ray diffraction method. The crystal is of orthorhombic, space group Pnma with a = 20.781(7), b = 6.857(2), c = 7.431(3) ?, V = 1058.8(6) ?3, Z = 4, Mr = 262.51, Dc = 1.647 g/cm3, λ = 0.71073 ?, μ(MoKα) = 0.833 mm? and F(000) = 528. The structure was refined to R = 0.0286 and wR = 0.0749 for 1073 1 observed reflections with I > 2σ(I). It exhibits a characteristic plane structure consisting of all atoms except Cl(2) and Cl(2)A. Two kinds of intermolecular hydrogen bonds are formed: N(1)– H(8A)…O(1) and N(1)–H(8A)…Cl(1). There also exist three kinds of π-π stacking in the crystal.展开更多
Due to the high electrophilic nature of azo-dienophiles, azo-Diels–Alder proceeds rapidly even without the need of a catalyst and is therefore regarded as the “click reaction”. This spontaneity causes strong backgr...Due to the high electrophilic nature of azo-dienophiles, azo-Diels–Alder proceeds rapidly even without the need of a catalyst and is therefore regarded as the “click reaction”. This spontaneity causes strong background reaction and poses a daunting challenge to chemists for developing the catalytic asymmetric version. Reported herein is the first catalytic asymmetric dearomative azo-Diels–Alder reaction between2-vinylindoles and triazoledione. This protocol makes use of the high energy barrier of dearomatization to avert the strong background reaction of azo-Diels–Alder reaction, allowing the implementation of the projected reaction at ambient temperature. Density functional theory calculations have been performed to gain insights into the reaction mechanism and the origins of the enantioselectivity. By using this method,a variety of tetracyclic indole derivatives have been readily prepared in good to excellent yields and with excellent diastereo-and enantio–selectivities(33 examples, up to 97% yield and >99% ee, >20:1 dr).展开更多
An efficient regioselective Friedel-Crafts hydroxyalkylation of N-substituted glyoxylamide with various indoles catalyzed by Lewis acids was developed. The reactions proceeded smoothly at room temperature and the 2-hy...An efficient regioselective Friedel-Crafts hydroxyalkylation of N-substituted glyoxylamide with various indoles catalyzed by Lewis acids was developed. The reactions proceeded smoothly at room temperature and the 2-hydroxy-2-（1H-indol-3-yl）-N-substituted acetamide resulted from the reactions catalyzed by FeSO4 were synthesized in excellent yields （up to 93%）. While the bisindole compounds were obtained when FeCl3 was used as a catalyst in excellent yields （up to 92%）. A possible mechanism was proposed.展开更多
A highly efficient and direct approach was developed to construct the structurally diverse spirooxindole skeleton,which is an important basic motif in natural products.Both the 3,30-pyrrolidonyl spirooxindoles and spi...A highly efficient and direct approach was developed to construct the structurally diverse spirooxindole skeleton,which is an important basic motif in natural products.Both the 3,30-pyrrolidonyl spirooxindoles and spiroindolin-2-one dlactones were 2smoothly obtained by the intramolecular Dieckmann cyclization of oxindoles in excellent yield under mild conditions.展开更多
3-（1-Ethyl-1H-indole-3-carbonyl）aminopropionic acid has been synthesized by alkylation of 3-（1H-indole-3-carbonyl）aminopropionic acid methyl ester with bromoethane,follo-wed by saponifying and acidating,in 89.0% y...3-（1-Ethyl-1H-indole-3-carbonyl）aminopropionic acid has been synthesized by alkylation of 3-（1H-indole-3-carbonyl）aminopropionic acid methyl ester with bromoethane,follo-wed by saponifying and acidating,in 89.0% yield.Its crystal structure was gotten and determined by X-ray diffraction method.The crystal is of orthorhombic,space group P212121 with a = 8.9490（12）,b = 11.1010（15）,c = 13.0475（18） ,V = 1296.2（3） 3,Z = 4,Dc = 1.334 g/cm3,λ = 0.71073 ,μ（MoKα） = 0.095 mm-1,Mr = 260.29 and F（000） = 552.The structure was refined to R = 0.0306 and wR = 0.1445 for 2612 observed reflections with I 2σ（I）.In the crystal structure,molecules are linked to each other through hydrogen bonds of N（2）-H（2）···O（1） and O（3）-H（3）···O（1）,generating a three-dimensional network.展开更多
文摘multi-component reaction was reported for the synthesis of 7-ester indoles and bis-indoles under microwave-assisted conditions,enriching and expanding the library of heterocyclic compounds.This reaction started from enamine ketone,aromatic ketone aldehyde hydrate,and carboxylic acid,and selectively synthesized 7-ester indoles and bis-indoles by changing the substituted enamine ketone substrate.This method had the characteristics of high regional selectivity,short reaction time,and green environmental protection.
文摘Skeletal editing has emerged as a powerful tool in organic chemistry,enabling the simplification of synthetic routes to complex molecules[1].Indoles,electron-rich nitrogen-containing building blocks,represent privileged scaffolds prevalent in pharmaceuticals,natural products,and bioactive compounds.The application of skeletal editing strategies to modify such structures is highly valuable and in growing demand.Leveraging the electronrich nature of indoles at C2 and C3,single-carbon atom insertion using cationic carbyne equivalents offers an efficient approach for indole ring expansion to quinoline(Scheme 1a).However,existing methods predominantly rely on halocarbene precursors,which restricts the functional groups of ring-expanded products to halogen[2],alkyl,aryl,heteroaryl and ester moieties[3].This limitation hinders their utility in late-stage skeletal modifications of complex targets.
文摘Indoles and their derivatives are an important class of N-heterocycles.In this article,iridium-catalyzed annulation reactions of N-aryl-2-aminopyridines to synthesize indole derivatives are designed and developed,which utilize vinylene carbonate as a new C2 synthon.This protocol is expected to provide a facile and useful access to various indole derivatives.
文摘Difluoromethyl compounds are widely found in natural products,bioactive molecule and pharmaceuticals.A visible-light induced difluoromethylation/cyclization of 2-aryl indoles is described to construct indolo[2,1-a]isoquinolin-6(5H)-one derivatives using the inexpensive and easy-to-handle HCF_(2)SO_(2)Na as an HCF2 sources.Diverse difluoromethylated indolo[2,1-a]isoquinolines were readily obtained in moderate to good yields.Mechanistic studies demonstrate that the reaction may involve a radical process.
文摘Indole[2,1-α]isoquinolines are an important class of bioactive molecules and show good antibacterial activity.In the present study,an efficient copper(I)-catalyzed acylation/cyclization has been developed for the construction of indolo[2,1-α]isoquinoline derivatives by utilizing 2-aryl-N-acryloyl indole and benzohydrazide as reactants in the presence of CuI as catalyst and tert-butyl hydroperoxide as oxidant.The present protocol exhibits good functional group tolerance,and a series of acylated indole[2,1-α]isoquinolines were synthesized in moderate to good yields.Radical trapping experiments indicated that the reaction may involve a radical process.
文摘Cycloheptatriene is a privileged structural motif present in many bioactive compounds,pharmaceutical agents and natural products,especially in a large number of core structures of sesquiterpenoids.Herein,a mild and efficient synthetic approach was reported for access of a series of C2 or C3-(cycloheptatrienyl)-substituted indoles.A wide range of functional groups can be well tolerated in this transformation,especially including hydroxyl,halo,carboxylic acid and its derivative groups.Based on these results,a rational mechanism via electrophilic substitution of indoles with tropylium tetrafluoroborate is proposed.
基金Supported by the Zhejiang Provincial Natural Science Foundation for Distinguished Young Scholar(No.LR20C190001)the National Natural Science Foundation of China(No.42376103)+1 种基金the Natural Science Foundation of Ningbo City(No.2021J062)the K.C.Wong Magna Fund in Ningbo University。
文摘Recently,more and more bacteria have been reported to become tolerant to antibiotics.In this study,one tnaA gene involved in indole production,and the effect of exogenous indole on the formation of persister cells specific to tetracycline in Vibrio splendidus were characterized.The tnaA Vs gene was first cloned and conditionally expressed in Escherichia coli Rosetta(DE3).To investigate the regulatory effect of TnaA Vs,the tnaA deletion strain AJ01/ΔtnaA was constructed by in-frame deletion.The undetected extracellular indole in the AJ01/ΔtnaA indicated that TnaA was the solo enzyme to produce indole in V.splendidus.The drop plate method showed that AJ01/ΔtnaA was more tolerant to the higher concentration of tetracycline than that of AJ01,being 340-fold higher in the proportion of survived cells when cell density OD 600≈0.65.Moreover,the synergistic effects of indole and tetracycline on killing of V.splendidus were determined.Results show that addition of 2-mmol/L indole increased the susceptibility of both AJ01 and AJ01/ΔtnaA to 10×minimum inhibitory concentration tetracycline.To explore the genes and pathways regulated by TnaA Vs,the transcriptomic analysis between AJ01 and AJ01/ΔtnaA was performed.Result shows that TCA cycle,arginine biosynthesis,quorum sensing and microbial metabolism in diverse environments were downregulated,while the ribosome pathways,the protein metabolic process,peptide biosynthetic and metabolic process were upregulated in the AJ01/ΔtnaA.This study shows that indole could enhance the bactericidal effect of tetracycline on V.splendidus by decreased ribosome level probably but increased ATP level.
基金Supported by Key Disciplines of The Sixth Cycle of Tongji Hospital,No.ZDTS24-BLShanghai Municipal Science and Technology Commission 2021"Science and Technology Innovation Action Plan"Medical Innovation Research Project,No.21Y11908800Clinical Research Project of Tongji Hospital of Tongji University,No.ITJ(ZD)2206.
文摘BACKGROUND Indolent T-cell lymphoma of the gastrointestinal tract(iTCL-GI)is a rare mature T-cell lymphoma that has been formally recognized as a distinct entity in the 5th Edition World Health Organization Classification of Tumours of Haematolymphoid Tumours.However,the coexistence of iTCL-GI with epithelial malignancies is rare in clinical practice.This study reports a case of iTCL-GI with gastric signet-ring cell carcinoma(SRCC).We aim to increase diagnostic awareness among clinicians and pathologists regarding multiple primary tumors.CASE SUMMARY A 65-year-old female presented with a 5-month history of lower abdominal pain,bloating,and vomiting.An abdominal computed tomography scan revealed irregular thickening of the gastric wall.Endoscopy revealed diffuse mucosal edema and rigid mucosa along the lesser curvature of the gastric body.There was a 1.5 cm mucosal protrusion on the greater curvature.Biopsy revealed that the lamina propria was expanded by a dense,nondestructive infiltrate of small lymphocytes in the greater curvature,which were characterized by a CD3+/CD8+/TIA-1+immunophenotype with a low Ki-67 index.Clonal T-cell receptor rearrangement was detected,but the Epstein-Barr virus encoded RNA's was negative.Lesions on the lesser curvature of the gastric body were confirmed to be SRCCs.After three months of follow-up,the patient completed four cycles of chemotherapy targeting the SRCC.While her abdominal pain improved,she experienced a weight loss of 5 kg.CONCLUSION Clinicians and pathologists must integrate assessment of these rare cases to prevent misdiagnosis and guide clinical practice.
基金Supported by The National High Level Hospital Clinical Research Funding,No.2022-PUMCH-B-132.
文摘BACKGROUND Indolent NK-cell lymphoproliferative disorder of the gastrointestinal tract(iNKLPD)is a rare and recently defined entity,recognized in the 2022 WHO classification of hematolymphoid tumors.iNKLPD typically exhibits a benign or slowly progressive clinical course,with disease localized to the gastrointestinal tract.Here,we present what we believe to be the first reported case of iNKLPD associated with protein-losing enteropathy(PLE),characterized by a poor response to chemotherapy and rapid clinical deterioration,culminating in death within a few months.CASE SUMMARY We report the case of a 64-year-old man who presented with bilateral lower-extremity edema and fatigue.Laboratory tests revealed marked hypoalbuminemia,while other liver function parameters remained within normal limits.Renal and cardiac function assessments were unremarkable.Histopathological examination of endoscopic biopsies confirmed a diagnosis of iNKLPD of the gastrointestinal tract.The patient was treated with oral prednisone and cyclosporine,which led to temporary improvement in both symptoms and serum albumin levels.However,disease relapse occurred during corticosteroid tapering,accompanied by worsening hypoalbu-minemia and refractory diarrhea.The patient died eight months after diagnosis,likely due to disease progression or severe treatment-related complications.CONCLUSION iNKLPD generally exhibits an indolent course;nonetheless,the prognosis may be poor if secondary PLE is involved.
基金Dr.P.L.More and Dr.W.N.Jadhav,Dnyanopasak College,Parbhani for providing necessary facilities and Financial support for this work by DST-SERC,New Delhi(SR/FT/CS- 023/2008) is highly appreciated
文摘An efficient protocol was developed for the synthesis of 3-aminoalkylated indoles using 3- chlorophenylboronic acid as a catalyst under ambient temperature conditions.The three-component reaction of indoles,aromatic aldehydes and N-methyl aniline offered corresponding 3-aminoalkylated indoles in excellent yields.This protocol presents some remarkable features such as mild reaction conditions,simple workup procedure and excellent yields.
基金the financial support from the Doctoral Research Fund of Henan University of Traditional Chinese Medicine
文摘Sulfamic acid was proved to be a cost-effective and recyclable catalyst for Friedel-Crafts type reaction of indole withα,β-unsaturated carbonyl compound and benzyl alcohol.Various indoles,α,β-unsaturated carbonyl compounds and a benzyl alcohol were successfully used in this type of reaction,and the corresponding products were obtained in good to excellent yields.
基金supported by the Knowledge Innovation Program of the CAS(No.KSCX2-YW-G-038, KSCX2-YW-G-027,29KZCX2-XB2-15-03),NSFC(No.30772636)NSFY(No.2005C0010Z)High-Tech Special Project of Yunnan Province(2007),and Foundation of Key State Lab.of Phytochemistry and Plant Resources in West China
文摘One new monoterpenoid indole alkaloid, l l-methoxyburnamine-17-O-3′,4′,5′-trimethoxybenzoate （1）, was isolated from Rauvolfia yunnanensis Tsiang. Its structure was identified by speclroscopic evidences.
文摘This work presents a new greener alternative for biocondensation of aldehydes and indoles for the synthesis of bis- and tris(indolyl)methanes catalyzed by lemon juice (Citrus limon) in good yields under ultrasound irradiation in aqueous ethanol. Various substituted aldehydes with indoles under this reaction condition are elucidated. Also, tetraindolyl compounds were prepared using terephthaldialdehyde by following the same protocol. This method is an environmentally benign, efficient reaction, which requires shorter reaction time and simple experimental and work-up procedures.
基金the National Natural Science Foundation of China(No.21672157)PAPD,the project of scientific and technologic infrastructure of Suzhou(No.SZS201708)+1 种基金Natural Science Foundation of Jiangsu Province(No.BK20200874)Natural Science Foundation for colleges and universities in Jiangsu Province(No.20KJD150001)。
文摘Herein,we reported a convenient and efficient multicomponent reaction of indoles,selenium powder and unactivated alkyl halides.This protocol provides a practical,and facile approach for the synthesis of 3-alkylselenindole derivatives.The advantages of this strategy include mild and transition-metal-free conditions,broad functional group tolerance,the use of simple and easily accessible seleniium powder and alkyl halides as coupling partners.More importantly,the reaction proceeded smoothly with a large scale(>10 g,>90%yield),which further highlighted the potential application of this selenation strategy.
基金The project was supported by the National 863 Program of China (No. 2001AA628100) and Natural Science Foundation of Guangdong Province (No. 31920)
文摘Trichloroacetyl) indole has been synthesized by the reaction of indole with trichloroacetyl chloride in 73% yield, and its crystal structure was determined by X-ray diffraction method. The crystal is of orthorhombic, space group Pnma with a = 20.781(7), b = 6.857(2), c = 7.431(3) ?, V = 1058.8(6) ?3, Z = 4, Mr = 262.51, Dc = 1.647 g/cm3, λ = 0.71073 ?, μ(MoKα) = 0.833 mm? and F(000) = 528. The structure was refined to R = 0.0286 and wR = 0.0749 for 1073 1 observed reflections with I > 2σ(I). It exhibits a characteristic plane structure consisting of all atoms except Cl(2) and Cl(2)A. Two kinds of intermolecular hydrogen bonds are formed: N(1)– H(8A)…O(1) and N(1)–H(8A)…Cl(1). There also exist three kinds of π-π stacking in the crystal.
基金the generous financial support from Natural Science Foundation of Henan Province (No.222300420084)application research plan of Key Scientific Research Projects in Colleges and Universities of Henan Province (No.22A150056)+1 种基金the Youth Innovation Team Program in Colleges and Universities of Shandong Province (No.2022KJ228)National Natural Science Foundation of China (No.22208302)。
文摘Due to the high electrophilic nature of azo-dienophiles, azo-Diels–Alder proceeds rapidly even without the need of a catalyst and is therefore regarded as the “click reaction”. This spontaneity causes strong background reaction and poses a daunting challenge to chemists for developing the catalytic asymmetric version. Reported herein is the first catalytic asymmetric dearomative azo-Diels–Alder reaction between2-vinylindoles and triazoledione. This protocol makes use of the high energy barrier of dearomatization to avert the strong background reaction of azo-Diels–Alder reaction, allowing the implementation of the projected reaction at ambient temperature. Density functional theory calculations have been performed to gain insights into the reaction mechanism and the origins of the enantioselectivity. By using this method,a variety of tetracyclic indole derivatives have been readily prepared in good to excellent yields and with excellent diastereo-and enantio–selectivities(33 examples, up to 97% yield and >99% ee, >20:1 dr).
基金the National Natural Science Foundation of China (Nos. 21472130, 81373259) for financial support of this study
文摘An efficient regioselective Friedel-Crafts hydroxyalkylation of N-substituted glyoxylamide with various indoles catalyzed by Lewis acids was developed. The reactions proceeded smoothly at room temperature and the 2-hydroxy-2-（1H-indol-3-yl）-N-substituted acetamide resulted from the reactions catalyzed by FeSO4 were synthesized in excellent yields （up to 93%）. While the bisindole compounds were obtained when FeCl3 was used as a catalyst in excellent yields （up to 92%）. A possible mechanism was proposed.
基金the Natural Science Foundation of Yunnan Province(2014FA008 and 2015FB167)the Program for Changjiang Scholars and Innovative Research Team in University(IRT13095).
文摘A highly efficient and direct approach was developed to construct the structurally diverse spirooxindole skeleton,which is an important basic motif in natural products.Both the 3,30-pyrrolidonyl spirooxindoles and spiroindolin-2-one dlactones were 2smoothly obtained by the intramolecular Dieckmann cyclization of oxindoles in excellent yield under mild conditions.
基金supported by the Natural Science Foundation of Guangdong Province (No.06300581)
文摘3-（1-Ethyl-1H-indole-3-carbonyl）aminopropionic acid has been synthesized by alkylation of 3-（1H-indole-3-carbonyl）aminopropionic acid methyl ester with bromoethane,follo-wed by saponifying and acidating,in 89.0% yield.Its crystal structure was gotten and determined by X-ray diffraction method.The crystal is of orthorhombic,space group P212121 with a = 8.9490（12）,b = 11.1010（15）,c = 13.0475（18） ,V = 1296.2（3） 3,Z = 4,Dc = 1.334 g/cm3,λ = 0.71073 ,μ（MoKα） = 0.095 mm-1,Mr = 260.29 and F（000） = 552.The structure was refined to R = 0.0306 and wR = 0.1445 for 2612 observed reflections with I 2σ（I）.In the crystal structure,molecules are linked to each other through hydrogen bonds of N（2）-H（2）···O（1） and O（3）-H（3）···O（1）,generating a three-dimensional network.
