Synthesis of nicotinamide and isonicotinamide derivatives via multicomponent reaction of alkyl isocyanides and acetylenic compounds in the presence of nicotinic or isonicotinic acid

被引：35

作者：

Alizadeh, Abdolali ^{[1
]}

Oskueyan, Qasem ^{[1
]}

Rostamnia, Sadegh ^{[1
]}

机构：

[1] Tarbiat Modares Univ, Dept Chem, Tehran, Iran

来源：

SYNTHESIS-STUTTGART | 2007年 / 17期

关键词：

alkyl isocyanide; dialkyl acetylenedicarboxyl ate; dibenzoylacetylene; nicotinic acid; isonicotinic acid; multicomponent reaction; zwitterion; nicotinamide; isonicotinamide; Dimroth-type rearrangement;

D O I：

10.1055/s-2007-983814

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An effective route to functionalized nicotinamide and isonicotinamide derivatives is described. This involves the reaction of nicotinic or isonicotinic acid with acetylenic compounds in the presence of alkyl isocyanides. The reactive 1:1 intermediates obtained from the addition of alkyl isocyanides to dialkyl acetylenedicarboxylates or dibenzoylacetylene was trapped by OH-acids such as nicotinic or isonicotinic acid to produce dialkyl 2-(alkylamino)5-[alkyl(3- or 4-pyridylcarbonyl)amino]-3,4-furandicarboxylate, N'(3)-(alkyl)-N-3-[3,4-dibenzoyl-5-(alkylamino)-2-furyl]nicotinamide, and N-4-(alkyl)-N-4- [3,4-dibenzoyl-5-(alkylamino)-2-furyl]isonicotinamide derivatives.

引用

页码：2637 / 2640

页数：4

共 23 条

[1] Reaction between tert-butyl isocyanide, dialkyl acetylenedicarboxylates, and aromatic carboxylic acids:: an efficient method for the synthesis of dialkyl (E)-2{[benzoyl(tert-butyl)amino]carbonyl}-2-butenedioate derivatives [J].