An Efficient Isocyanide‐Based Three‐Component Diastereoselective Synthesis of Chromane‐3,4‐dicarboxamides

Abstract

An efficient method for the diastereoselective synthesis of chromane‐3,4‐dicarboxamides via the three‐component reaction of 2‐oxo‐2H‐chromene‐3‐carboxylic acids, amines, and isocyanides in MeCN is 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 .…”

“…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 As a matter of fact, the unique features of these compounds make them good candidates for being selected for the synthesis of divergent types of heterocycles.…”

Diastereoselective One‐Pot Synthesis of Coumarin‐4‐carboxamido‐3‐esters via a Four‐Component Isocyanide‐Based Reaction and Molecular Docking Study

“…Continuing our efforts directed toward the straightforward preparation of biologically interesting heterocycles through IMCRs,, in this study, we report a facile and efficient four‐component stereoselective reaction between 2‐hydroxybenzaldehyde (salicylaldehyde) 1 , malonic acid 2 , alkyl or aryl isocyanides 3 and various alcohols 4 for the preparation of a new series of coumarin‐4‐carboxamido‐3‐esters 5 (Scheme ). Although in some research IMCRs method was utilized for the synthesis of dihydrocoumarin derivatives,, to the best of our knowledge, there is no report on the preparation of dihydrocoumarins via four‐component condensation reactions of 2‐hydroxybenzaldehyde with malonic acid in the presence of isocyanides and alcohols.…”