Catalyst-free synthesis of functionalized dihydro-2-oxypyrroles by the reaction of enaminones and N,N′-bis(phenylmethylidene)phenylmethane

Abstract

A catalyst-free and convenient approach for the preparation of substituted dihydro-2oxypyrrole is described. This three-component reaction between primary amines, dialkyl acetylenedicarboxylate, and N,N 0 -bis(phenylmethylidene)phenylmethane proceeds in MeOH under reflux conditions in good to excellent yields.

Nano-TiCl4/SiO2: an efficient catalyst for the one-pot synthesis of highly substituted dihydro-2-oxopyrroles

“…Recently, a few methods have been reported for the synthesis of dihydro-2-oxopyrroles via MCRs such as catalyst-free reaction of enaminones with N,N 0 -bis(phenylmethylidene) [28], catalyst-free/AcOH [29], and in the presence of I 2 [30], AcOH/NEt 3 [31], Cu(OAc) 2 [35], and InCl 3 [36]. Considering that, some of these procedures have drawbacks, such as high reaction temperature, long reaction times, and tedious work-up condition like utilizing column chromatography.…”

N,N′‐Bis(arylmethylidene)arylmethanediamines: Suitable Precursors for the Synthesis of 1‐Pyrroline Derivatives

“…Previously, our research group has reported divers multicomponent reactions (MCRs) for generating some aza‐cyclic compounds using N , N′ ‐bis(phenylmethylidene)‐phenylmethanediamines . In continuation and considering the importance of the 1‐pyrroline scaffold, we describe in this article a one‐pot, three‐component reaction of phenacylbromide derivatives 1 , malononitrile, and N , N′ ‐bis(arylmethylidene)‐arylmethanediamines 2 in the presence of Et 3 N as catalyst in EtOH to afford 4,5‐dihydro‐5‐hydroxy‐3 H ‐pyrrole‐3,3‐dicarbonitrile derivatives 3 in high yields ( Scheme ).…”

A simple and green approach for the synthesis of polyfunctionalized mono- and bis-dihydro-2-oxopyrroles catalyzed by trityl chloride

“…1). [10][11][12][13][14][15][16] These heterocycles and derivatives are also active and important reagents as a material for the synthesis of organic complexes. 17 As a result, several methods have been developed to synthesize these useful heterocycles.…”

“…17 As a result, several methods have been developed to synthesize these useful heterocycles. 16,[18][19][20][21][22] Recently, Zhu et al have reported an efficient multi-component synthesis of highly functionalized dihydro-2-oxopyrroles via reaction of amines, acetylenic esters and aldehydes in the presence of acetic acid as catalyst. However, the reactions were carried out in the presence of 200 mol% of catalyst at 70 C and products puried by preparative TLC.…”