A convenient route for the conversion of inosine to the corresponding 6-amino, 6-methoxy and 6-ethoxy derivatives is reported. This conversion can be achieved by ammoniation or etherification of the 6-pyridinium inter...A convenient route for the conversion of inosine to the corresponding 6-amino, 6-methoxy and 6-ethoxy derivatives is reported. This conversion can be achieved by ammoniation or etherification of the 6-pyridinium intermediate(3) which can be readily produced under mild reaction conditions. The chemistry and characterization of these compounds are presented, A plausible mechanism of the reaction is proposed.展开更多
An efficient triethylamine-catalyzed synthesis of 4-amino-3,5-dicyano-6-arylphthalates is described.A one-pot,simple pseudo four-component reaction between arylaldehydes,dialkyl acetylenedicarboxylates, and twice as m...An efficient triethylamine-catalyzed synthesis of 4-amino-3,5-dicyano-6-arylphthalates is described.A one-pot,simple pseudo four-component reaction between arylaldehydes,dialkyl acetylenedicarboxylates, and twice as much malononitrile gave 4-amino-3,5-dicyano-6-arylphthalates in good to excellent yields.展开更多
Solubility of 2-amino-6-chloropurine in Mitsunobu solvents could be significantly improved after its exocyclic amino group is protected via N-tert-butoxycarbonylation.The bis-Boc protected 2-amino-6-chloropurine also ...Solubility of 2-amino-6-chloropurine in Mitsunobu solvents could be significantly improved after its exocyclic amino group is protected via N-tert-butoxycarbonylation.The bis-Boc protected 2-amino-6-chloropurine also shows excellent activity and N9 selectivity in the coupling with various alcohols by a Mitsunobu reaction.Then,a new practical and efficient method is established for the synthesis of penciclovir(PCV) from bis-Boc-2-amino-6-chloropurine 9 and the side chain of 5-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxane 5—the latter being a more easily prepared cyclic precursor of the diacetate side chain used in the conventional process.The coupling of 9 with 5 proceeded regioselectively at a N9 position of purine derivative for a good yield under Mitsunobu conditions.展开更多
The reaction mechanism of 2-methoxybenzaldehyde, 4-bromo-indanone, malononitrile and ammonium acetate one-pot to form 6-（2-methoxyphenyl）-2-amino-6-bromo-5 Hindeno[1,2-b]pyridine-3-carbonitrile was studied by densit...The reaction mechanism of 2-methoxybenzaldehyde, 4-bromo-indanone, malononitrile and ammonium acetate one-pot to form 6-（2-methoxyphenyl）-2-amino-6-bromo-5 Hindeno[1,2-b]pyridine-3-carbonitrile was studied by density functional theory. The geometries of the reactants, transition states, intermediates and products were optimized at the PW91/DNP level. Vibration analysis was carried out to confirm the transition state structure. Reaction pathways were investigated in this study. The result indicates that the reaction Re→ TSB1→IMB1→ TSB2→ IMB2→TSB3→IMB3→TSB4→IMB4→TSB5→IMB5→TSB6→IMB6→TSB7→IMB7→ TSB8→IMB8→TSB9→IMB9→P2 is the main pathway, the activation energy of which is the lowest. The dominant product predicted theoretically is in agreement with the experiment results.展开更多
A facile procedure for the synthesis of 3-（2′-amino-3′-cyano-4′-arylpyrid-6′-yl） coumarins are being reported starting from 3- acetylcoumarin, aromatic aldehydes and malononitrile. The reactions were carried out...A facile procedure for the synthesis of 3-（2′-amino-3′-cyano-4′-arylpyrid-6′-yl） coumarins are being reported starting from 3- acetylcoumarin, aromatic aldehydes and malononitrile. The reactions were carried out on microwave irradiation in good yield with short time and easy work-up. The structures of all the compounds have been confirmed on the basis of their analytical, IR, ^1H NMR, and mass spectral data.展开更多
4-Amino-3-mercapto-6-methyl-l,2,4-triazin-5（4H）-one 1 converted to 4-amino-6-methy-3-（methylthio）-1,2,4-triazin-5（4H）-one by methylation with methyl iodide.Controlled hydrazination of the resulting compound affo...4-Amino-3-mercapto-6-methyl-l,2,4-triazin-5（4H）-one 1 converted to 4-amino-6-methy-3-（methylthio）-1,2,4-triazin-5（4H）-one by methylation with methyl iodide.Controlled hydrazination of the resulting compound afforded 4-amino-3-hydrazinyl-6- methyl-l,2,4-triazin-5（4H）-one 2 as a building block,to the synthesis of some novel derivatives of[1,2,4]triazino- [4,3,b][1,2,4,5]tetrazepine 3-6,by the reaction with 3-chloropentane-2,4-dione,chloro acetonitrile,1,3-dichloroacetone,and methyl bromoacetate.This general synthetic procedure can be extended to the preparation of wide variety of tetrazepines using 1,2- bielectrophiles derivatives.展开更多
文摘A convenient route for the conversion of inosine to the corresponding 6-amino, 6-methoxy and 6-ethoxy derivatives is reported. This conversion can be achieved by ammoniation or etherification of the 6-pyridinium intermediate(3) which can be readily produced under mild reaction conditions. The chemistry and characterization of these compounds are presented, A plausible mechanism of the reaction is proposed.
基金the financial support from the Research Council of Payame Noor University(PNU),Abhar-lran, and my colleague Ismail Hasani Asl
文摘An efficient triethylamine-catalyzed synthesis of 4-amino-3,5-dicyano-6-arylphthalates is described.A one-pot,simple pseudo four-component reaction between arylaldehydes,dialkyl acetylenedicarboxylates, and twice as much malononitrile gave 4-amino-3,5-dicyano-6-arylphthalates in good to excellent yields.
文摘Solubility of 2-amino-6-chloropurine in Mitsunobu solvents could be significantly improved after its exocyclic amino group is protected via N-tert-butoxycarbonylation.The bis-Boc protected 2-amino-6-chloropurine also shows excellent activity and N9 selectivity in the coupling with various alcohols by a Mitsunobu reaction.Then,a new practical and efficient method is established for the synthesis of penciclovir(PCV) from bis-Boc-2-amino-6-chloropurine 9 and the side chain of 5-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxane 5—the latter being a more easily prepared cyclic precursor of the diacetate side chain used in the conventional process.The coupling of 9 with 5 proceeded regioselectively at a N9 position of purine derivative for a good yield under Mitsunobu conditions.
基金Project supported by the Scientific and Technological Research Program of Chongqing Municipal Education Commission(KJ1601215,KJ15012002)the Ministry of Education “Chunhui Plan”(Z2016177)
文摘The reaction mechanism of 2-methoxybenzaldehyde, 4-bromo-indanone, malononitrile and ammonium acetate one-pot to form 6-（2-methoxyphenyl）-2-amino-6-bromo-5 Hindeno[1,2-b]pyridine-3-carbonitrile was studied by density functional theory. The geometries of the reactants, transition states, intermediates and products were optimized at the PW91/DNP level. Vibration analysis was carried out to confirm the transition state structure. Reaction pathways were investigated in this study. The result indicates that the reaction Re→ TSB1→IMB1→ TSB2→ IMB2→TSB3→IMB3→TSB4→IMB4→TSB5→IMB5→TSB6→IMB6→TSB7→IMB7→ TSB8→IMB8→TSB9→IMB9→P2 is the main pathway, the activation energy of which is the lowest. The dominant product predicted theoretically is in agreement with the experiment results.
基金the Jiangsu Key Laboratory for Chemistry of Low-Dimensional Materials for financial support(No.JSKC07041).
文摘A facile procedure for the synthesis of 3-（2′-amino-3′-cyano-4′-arylpyrid-6′-yl） coumarins are being reported starting from 3- acetylcoumarin, aromatic aldehydes and malononitrile. The reactions were carried out on microwave irradiation in good yield with short time and easy work-up. The structures of all the compounds have been confirmed on the basis of their analytical, IR, ^1H NMR, and mass spectral data.
文摘4-Amino-3-mercapto-6-methyl-l,2,4-triazin-5（4H）-one 1 converted to 4-amino-6-methy-3-（methylthio）-1,2,4-triazin-5（4H）-one by methylation with methyl iodide.Controlled hydrazination of the resulting compound afforded 4-amino-3-hydrazinyl-6- methyl-l,2,4-triazin-5（4H）-one 2 as a building block,to the synthesis of some novel derivatives of[1,2,4]triazino- [4,3,b][1,2,4,5]tetrazepine 3-6,by the reaction with 3-chloropentane-2,4-dione,chloro acetonitrile,1,3-dichloroacetone,and methyl bromoacetate.This general synthetic procedure can be extended to the preparation of wide variety of tetrazepines using 1,2- bielectrophiles derivatives.
