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一锅法合成2，4，6-三氯喹唑啉和6-硝基-2，4-二氯喹唑啉 被引量：2

One-pot Synthesis of 2,4,6-Trichloroquinazoline and 2,4-Dichloro-6-nitroquinazoline
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摘要 在五氯化磷的存在下,2-氨基-5-氯苯甲酸(1a)或2-氨基-5-硝基苯甲酸(1b)与尿素缩合,一锅法合成了2,4,6-三氯喹唑啉(2a)或6-硝基-2,4-二氯喹唑啉(2b),其结构经1H NMR和ESI-MS表征。合成2a的最佳反应条件为:1a2.5 mmol,n(1a)∶n(PC l5)∶n(尿素)=1.0∶6.0∶2.2,回流反应1 h,收率41%。 2,4,6-Trichloroquinazoline（2a） or 2,4-dichloro-6-nitroquinazoline （2b） was synthesized by the condensation of urea with 2-amino-5-chlorobenzoic acid（1a） or 2-amino-5-nitrobenzoic acid（1b） in the presence of phosphorus pentachloride in one-pot reaction. The structures were characterized by 1H NMR and ESI-MS. The optimal reaction conditions of synthesizing 2a in yield of 41% were follows： la was 2.5 retool; n（1a） ：n（PCl5） ： n（urea） was 1.0：6.0：2.2; reflux time was 1.0 h.
作者 张崇敬 张志辉 徐柏玲 王玉玲
机构地区 中国医学科学院北京协和医学院药物研究所 沈阳药科大学制药工程学院
出处 《合成化学》 CAS CSCD 2008年第6期673-675,共3页 Chinese Journal of Synthetic Chemistry
基金 国家自然科学基金资助项目(30500643)
关键词 喹唑啉 五氯化磷 尿素 一锅反应 合成 quinazoline phosphorus pentachloride urea one-pot reaction synthesis
分类号 O626.4 [理学—有机化学]
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参考文献18

  • 1Curd F H S, Landquist J K, Rose F L. Synthetic antimalarials. Part ⅩⅣ. Some 2-arylamino-4-aminoalkylaminoquinazolinos[ J]. J Chem Soc, 1947:775 - 783.
  • 2Xu G F, Song B A, Bhadury P S, et al. Synthesis and antifungal activity of novel S-substituted 6-fluoro-4-alkyl (aryl) thioquinazoline derivatives [ J ]. Bioorg Med Chem,2007,15:3768 - 3774.
  • 3Alagarsamy V, Salomon V R, Vanikavitha G, et al. Synthesis, analgesic, anti-inflammatory and antibacterial activities of some novel 2-phenyl-3-substitued quinazolin-4 (3H) ones [ J]. Biol Pharm Bull, 2002,25: 1432 - 1435.
  • 4Hayao S, Havera H J, Strycker W G, et al. New sedative and hypotensive 3-substituted-2, 4 ( 1H, 3H)- quinazoliones [ J ]. J Med Chem, 1965,8 : 807 - 811.
  • 5Ram V J, Farhanullah, Tfipathi B K, et al. Synthesis and antihyperglycemic activity of suitably functionalized 3H-quinazolin-4-ones [ J ]. Bioorg Med Chem, 2003,11:2439 -2444.
  • 6Luth A, Lowe W. Synthesis of 4-( indole-3-yl-quinazolines-A new class of epidermal growth factor tyrosine kinase inhibitors[ J]. Eur J Med Chem ,2008,43 :1478 - 1488.
  • 7EI-Brollosy N R. Synthesis of new quinazoline-2,4- (1H, 3H)-diane non-nucleoside analogues of the reverse transcriptase inhibitor TNK-651 [ J ]. J Chem Res ,2007:358 - 361.
  • 8Witt A, Bergman J. Recent developments in the field of quinazoline chemistry[ J ]. Curr Org Chem 2003,7: 659 - 677.
  • 9Connolly D J, Cusack D, O' Sullivan T P, et al. Synthesis of quinazolinones and quinazilines [ J ]. Tetrahedron,2005,61 : 10153 - 10202.
  • 10刘刚,李晓燕.喹唑啉类化合物合成新方法研究进展[J].化工时刊,2007,21(11):47-57. 被引量：1

二级参考文献36

  • 1张建华.喹唑啉类降压药物中有关中间体的合成技术综译[J].北京医药,1994(2):22-31. 被引量：1
  • 2蒙小英,张秀平,李炳生,李高德.2,4-二氨基-5-甲基-6-取代苄氨基喹唑啉衍生物的合成及其抗疟和抗肿瘤作用[J].药学学报,1989,24(8):578-586. 被引量：5
  • 3黄润秋,李慧英,马军安,邱德文.4－肟醚基喹唑啉类化合物的合成及其抗植物病毒TMV活性[J].高等学校化学学报,1996,17(4):571-574. 被引量：23
  • 4Blank J, Kandt M,Pfeiffer W D,et al. Domino cyellzation of 2-isothiocyanatobenzonitrile with carboxylic hydrazides one-pot synthesis of 1,2,4-triazolo[1,5-c] quinazoline-5(6H)-thione[J].Eur.J.Org.Chem,2003,(1):182-189.
  • 5Visnjevac A, Tusek-Bozic L, Majeric-Elenkov M,et al. Copper(II)-promoted cheical transformations of 3-substituted 5-(2'-pyridyl)-1,4-benzodiazepin-2 -one derivatives crystal structures and specteoscopic characterization of metal complexes[J].Eur.J.Inorg. Chem, 2001,(10): 2647-2654.
  • 6Lim J K, Negash K, Hanraham S M,et al. Synthesis of 4-(3'-[125 I]iodoanilino)-6,7-dialkoxyqunazolines:radiolabeled epidermal growth factor receptor tyrosine kinase inhibitors [J]. J,Labelled Compd. Radiopharm,2000, 43(12):1183-1191.
  • 7Matheson S L, Mzengeza S, Jean-Claude B J. Synthesis of 1-[4-(m-tolyl)amino -6-quinazolinyl]-3-[14C]-methyl triazene: a radiolabeled probe for the combi-targeting concept [J]. J. Labelled. Compd. Radiopharm,2003,46(8):729-735.
  • 8Lee J Y, Park Y K, Seo S H,et al.1,4-Dioxane-fused 4-anilinoquinazoline as inhibitors of epidermal growth factor receptor kinase [J]. Arch. Pharm (Weinheim).2001,334:357-360.
  • 9Lee J Y, Lee Y S, Park H K., et al. 4-(Phenylamino) [1,4] dioxano[2,3-g] quinazoline derivatives and process for preparing the same [P].US 2003045537, 2003-03-06.
  • 10Ibrahim S S, Abdel-Halim A M, Gabr Y, et al. Synthesis and biological evaluation of some new fused quinazoline derivatives[J]. J. Chem. Res.Synop, 1997,(5):154-155.

同被引文献32

  • 1KANTEVARI S, VUPPALAPATI S V N, BIRADAR D O, et al. Highly Efficient, One-pot, Solvent-free Synthesis of Tetrasu- bstituted Imidazoles Using HC104-SiOz as Novel Heterogeneous Catalyst [J]. J Mol Catal A: Chem, 2007,266 : 109-113.
  • 2SADEGHI B,MIRJALIL 15 B F, HASHEMI M M. ISF-SiO2An Efficient Reagent System for the One-pot Synthesis of 1,2,4,5-tetrasubstituted Imidazoles [J]. Tetrahedron Lett, 2008,49 : 2575-2577.
  • 3SHARMA S D, HAZARIKA P,KONWAR D. An Efficient and One-pot Synthesis of 2,4,5-trisubstituted and 1,2,4,5- tetrasubstituted Imidazoles Catalyzed by InCl3· 3 Hz O I-J]. Tetrahedron Lett, 2008,49 : 2216-2220.
  • 4SAFARI J ,KHALILI S D,BANITABA S H. A Novel and an Efficient Catalyst for One-pot Synthesis of 2,4,5-trisubsti- tuted Imidazoles by Using Mihrowave Irradiation Under Solvent-free Conditions [J]. j Chem Sci,2010,122(3):437-441.
  • 5RAJAPAKS E H A,ZHU H,YOUNG M B,et al. A Mild and Efficient One Pot Synthesis of 1,3,4-oxadiazoles from Car- boxylic Add.s and Aeyl Hydrazides [J]. Tetrahedron Lett,2006,47:4827-4830.
  • 6STABILE P, LAMONICA A,RIBECAI A, et al. Mild and Convenient One-pot Synthesis of 1,3,4-oxadiazoles [J]. Tet- rahedron Lett, 2010,51 : 4801-4805.
  • 7KUMAR D,VADDULA B R,CHANG K H ,et al. One-pot Synthesis and Anticancer Studies of 2-arylamino-5-aryl-1,3, .1 -thiadiazoles [J]. Bioorg Med Chem Lett, 2011,21 : 2320-2323.
  • 8ZHANG Dongnuan, LI Jitai,SONG Yali, et al. Efficient One-pot Three-component Synthesis of N-(4-arylthiazol-2-yl) Hydrazones in Water Under Ultrasound Irradiation [J]. Ultrason Sonochem,2012,19:475-478.
  • 9RAO V K,CHHIKARA B S, SHIRAZI A N,et al. 3-substitued Indoles:One-pot Synthesis and Evaluation of Anticancer and Src Kinase Inhibitory Activities [J]. Bioorg Med Chem Lett,2011,21:3511-3514.
  • 10KO Shengkai, YAO Chingfa. Ceric Ammonium Nitrate (CAN) Catalyzes the One-pot Synthesisof Polyhydroquinoline via the Hantzseh Reaction [J]. Tetrahedron, 2006,62 : 7293-7299.

引证文献2

合成化学
2008年 第6期

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