Isocyanide-Based Multicomponent Reactions: Synthesis of Alkyl-2-(1-(alkylcarbamoyl)-2,2-dicyanoethyl)benzoate and Isochromeno[3,4-b]pyrrole Derivatives

Abstract

A novel four-component reaction between 2-formylbenzoic acids, malononitrile, isocyanides, and alcohols has been developed for a highly efficient preparation of alkyl-2-(1-(alkylcarbamoyl)-2,2-dicyanoethyl)benzoate derivatives. This high atom economy reaction led to the construction of two carbon-carbon bonds, one amide, and one ester group in a single synthetic step. Furthermore, a three-component reaction between 2-formylbenzoic acids, malononitrile, and isocyanides in dichloromethane for the preparation of isochromeno[3,4-b]pyrroles has been reported.

Isocyanide-based multicomponent reactions in the synthesis of heterocycles

“…The organic segment is connected to the isocyanide group via the nitrogen atom, not via the carbon. They are used as privileged synthons for the synthesis of other organic compounds in particular various heterocycles [23][24][25][26][27][28][29][30][31][32][33][34][35][36][37] , frequently via multicomponent reactions (MCRs) namely isocyanide multicomponent reactions (IMCRs) 25,[38][39][40][41][42][43][44][45][46][47][48][49] . Noticeably isocyanides are susceptible to polymerization 50 .…”

Aldo‐X Bifunctional Building Blocks for the Synthesis of Heterocycles

“…An isochromeno[3,4 ‐b ]pyrrole derivative 127 was synthesized by Soleimani and Zainali through a three‐component reaction of 112 a , malononitrile, and isocyanide by using Na 2 CO 3 as a catalyst and dichloromethane as a solvent (Scheme ) …”

A convenient one-pot synthesis of novel tetraamides via 2-cyclopentylidenemalonic acid based Ugi-four component reaction

“…The Ugi strategy offers important advantages over classical stepwise approaches and designs several bonds and construction of complex molecular architectures from simple precursors in a one-pot reaction without any need for isolating intermediates [21][22][23][24]. The most important part of Ugi reaction is carried out through the reaction of an amine, carbonyl compound, carboxylic acid, and isocyanide, which has generated a much interesting product with potential and capacity to generate highly diverse products of biological and medicinal relevance; i.e.…”