Copper(I)-catalyzed cascade sulfonimidate to sulfonamide rearrangement: synthesis of imidazo[1,2-a][1,4]diazepin-7(6H)-one

Muthupandi Nagaraj; Muthusamy Boominathan; Devanathan Perumal; Shanmugam Muthusubramanian; Nattamai Bhuvanesh

doi:10.1021/jo300855f

Copper(I)-catalyzed cascade sulfonimidate to sulfonamide rearrangement: synthesis of imidazo[1,2-a][1,4]diazepin-7(6H)-one

J Org Chem. 2012 Jul 20;77(14):6319-26. doi: 10.1021/jo300855f. Epub 2012 Jun 29.

Authors

Muthupandi Nagaraj¹, Muthusamy Boominathan, Devanathan Perumal, Shanmugam Muthusubramanian, Nattamai Bhuvanesh

Affiliation

¹ Department of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625 021, India.

PMID: 22721359
DOI: 10.1021/jo300855f

Abstract

A novel strategy of copper(I)-catalyzed cascade intramolecular nucleophilic attack on N-sulfonylketenimine followed by rearrangement of sulfonimidates to sulfonamides resulting in a library of substituted 8,9-dihydro-5H-imidazo[1,2-a][1,4]diazepin-7(6H)-ones has been developed.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Azepines / chemistry*
Catalysis
Copper / chemistry*
Cyclization
Imidazoles / chemistry*
Molecular Structure
Sulfonamides / chemical synthesis*
Sulfonamides / chemistry

Substances

Azepines
Imidazoles
Sulfonamides
imidazo(1,2-a)(1,4)diazepin-76H-one
Copper