Rh-Catalyzed Denitrogenative Reaction of N-Sulfonyl-1,2,3-triazoles with Isatoic Anhydrides and Oxadiazolones

Kuntal Pal; Abdul Hoque; Chandra M R Volla

doi:10.1002/chem.201705036

Rh-Catalyzed Denitrogenative Reaction of N-Sulfonyl-1,2,3-triazoles with Isatoic Anhydrides and Oxadiazolones

Chemistry. 2018 Feb 21;24(11):2558-2564. doi: 10.1002/chem.201705036. Epub 2017 Dec 5.

Authors

Kuntal Pal¹, Abdul Hoque¹, Chandra M R Volla¹

Affiliation

¹ Department of Chemistry, Indian Institute of Technology-Bombay, Powai, Mumbai, 400076, India.

PMID: 29131423
DOI: 10.1002/chem.201705036

Abstract

A convenient and simple, Rh^II -catalyzed denitrogenative method for the synthesis of biologically interesting 2-amino-benzoxazinones and 5-amino-oxadiazoles from readily available isatoic anhydrides and oxadiazolones has been developed. These reactions proceed via an O-H insertion onto α-imino Rh^II -carbenoid species followed by a rearrangement. The scope of the reaction can also be extended to benzoxazinones to access amino-substituted benzoxazines.

Keywords: benzoxazinones; isatoic anhydride; nitrogen; rhodium; triazoles.