One-step, three-component synthesis of pyridines and 1,4-dihydropyridines with manifold medicinal utility

被引:207
作者
Evdokimov, NM [1 ]
Magedov, IV
Kireev, AS
Kornienko, A
机构
[1] Timiryazev Agr Acad, Dept Organ Chem, Moscow 127550, Russia
[2] Intelbioscan Ltd, Moscow 127550, Russia
[3] New Mexico Inst Min & Technol, Dept Chem, Socorro, NM 87801 USA
关键词
D O I
10.1021/ol052994+
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Privileged medicinal scaffolds based on the structures of 2-amino-3,5-dicyano-6-sulfanylpyridines and the corresponding 1,4-dihydropyridines have been prepared via a single-step, three-component reaction of structurally diverse aldehydes with various thiols and malononitrile. Mechanistic studies revealed that 1,4-dyhidropyridines undergo oxidation by the intermediate Knoevenagel adducts rather than by air oxygen. Although the latter process undermines the yields of pyridines, it results in the formation of substituted enaminonitriles, promising antiinflammatory agents.
引用
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页码:899 / 902
页数:4
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