Recent applications of aziridine ring expansion reactions in heterocyclic synthesis

Abstract

The inherent reactivity of the aziridine ring due to ring-strain makes it valuable building blocks for the synthesis of other heterocyclic motifs of biological relevance. Of particular significance is the generation of azomethine ylides from them and cycloaddition of ylides with alkenes, alkynes, and heterocumulenes. The ring undergoes opening followed by cyclization with a variety of reagents either in the presence of a catalyst or without any catalyst. This review article discusses the recent applications of aziridines in syntheses of four-to seven-membered heterocycles of biological relevance such as azetidines, 2

Stereocontrolled Synthesis of Functionalized Azaheterocycles from Carbocycles through Oxidative Ring Opening/Reductive Ring Closing Protocols

“…A large number of synthetic methodologies have been developed to the access of azaheterocycles including aziridines, azetidines, pyrrolidines, piperidines or azepanes . In organic and pharmaceutical chemistry, the creation of novel saturated N ‐heterocycles is a field explored deeply.…”

“…A large number of synthetic methodologies have been developed to the access of azaheterocycles including aziridines, azetidines, pyrrolidines, piperidines or azepanes. [31][32][33][34][35] In organic and pharmaceutical chemistry, the creation of novel saturated N-heterocycles is a field explored deeply. However, due to the increasing importance of these scaffolds, the development of novel, efficient, cost effective, selective, and stereocontrolled protocols for these derivatives is a continuous challenge in modern chemistry.…”

Exploring the chemical space and the bioactivity profile of lactams: a chemoinformatic study

“…The most common lactams are four-membered (b-lactams, also known as 2-azetidinones, Fig. 1a), 1,[5][6][7][8] vemembered (g-lactams, also known as 2-pyrrolidinones, Fig. 1b), 2,9-11 six-membered (d-lactams, also known as 2-piperidinones, Fig.…”

Highly Stereoselective Synthesis of Isoindole Derivatives Containing an Azetidinone Ring

“…[10][11][12][13][14] Less commonly, they are also used to prepare six-membered rings. [15][16][17][18][19][20][21][22][23][24] Although azetidin-2-ones have been extensively investigated, our literature surveys revealed that isoindoles bearing a β-lactam ring at the β-position had not been reported. We therefore decided to synthesize such compounds in a highly stereoselective manner by in situ production of a novel ketene that would subsequently be trapped with various Schiff bases, and an electrocyclic reaction of a zwitterionic intermediate.…”