A simple and convenient synthesis of tautomeric (6 or 2)-hydroxy-4-methyl-(2 or 6)-oxo-1-(substituted phenyl)-(1,2 or 1,6)-dihydropyridine-3-carbonitriles

被引：4

作者：

Ajaj, Ismail ^{[1
]}

Mijin, Dusan ^{[1
]}

Maslak, Veselin ^{[2
]}

Brkovic, Danijela ^{[1
]}

Milcic, Milos ^{[2
]}

Todorovic, Nina ^{[3
]}

Marinkovic, Aleksandar ^{[1
]}

机构：

[1] Univ Belgrade, Fac Technol & Met, Belgrade 11120, Serbia

[2] Univ Belgrade, Fac Chem, Belgrade 11000, Serbia

[3] Univ Belgrade, Inst Chem Technol & Met, Ctr Chem, Belgrade 11000, Serbia

来源：

MONATSHEFTE FUR CHEMIE | 2013年 / 144卷 / 05期

关键词：

Microwave assisted synthesis; Heterocycles; Cyclizations; Ab initio calculations; Tautomerism; MICROWAVE-ASSISTED SYNTHESIS; STRUCTURE-BASED DESIGN; BIOLOGICAL EVALUATION; INHIBITORS; 2-PYRIDONES; CHEMISTRY; AGENTS; DYES; NMR;

D O I：

10.1007/s00706-012-0911-5

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A simple and convenient synthesis of tautomeric (6 or 2)-hydroxy-4-methyl-(2 or 6)-oxo-1-(substituted phenyl)-(1,2 or 1,6)-dihydropyridine-3-carbonitriles from ethyl acetoacetate and 2-cyano-N-(substituted phenyl)ethanamides using microwave-assisted chemistry is presented. The structure of the obtained product was confirmed by the use of FT-IR, NMR, UV, and MS techniques. The presence of tautomeric forms (6-hydroxy-4-methyl-2-oxo-1-(substituted phenyl)-1,2-dihydropyridine-3-carbonitrile and 2-hydroxy-4-methyl-6-oxo-1-(substituted phenyl)-1,6-dihydropyridine-3-carbonitrile) and the state of equilibrium of the obtained product in DMSO-d (6) was studied by H-1 and C-13 NMR spectroscopy, as well as B3LYP/6-311++G(d,p) and GIAO/WP04/aug-cc-pVDZ theoretical calculations.

引用

页码：665 / 675

页数：11

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