Synthesis of cis-β-Amidevinyl Benziodoxolones from the Ethynyl Benziodoxolone-Chloroform Complex and Sulfonamides

Daisuke Shimbo; Atsushi Shibata; Masaharu Yudasaka; Toshifumi Maruyama; Norihiro Tada; Bunji Uno; Akichika Itoh

doi:10.1021/acs.orglett.9b03990

Synthesis of cis-β-Amidevinyl Benziodoxolones from the Ethynyl Benziodoxolone-Chloroform Complex and Sulfonamides

Org Lett. 2019 Dec 6;21(23):9769-9773. doi: 10.1021/acs.orglett.9b03990. Epub 2019 Nov 19.

Authors

Daisuke Shimbo¹, Atsushi Shibata¹, Masaharu Yudasaka¹, Toshifumi Maruyama², Norihiro Tada¹, Bunji Uno¹, Akichika Itoh¹

Affiliations

¹ Gifu Pharmaceutical University 1-25-4, Daigaku-nishi , Gifu 501-1196 , Japan.
² Department of Chemistry and Biomolecular Science, Faculty of Engineering , Gifu University , Yanagido 1-1 , Gifu 501-1193 , Japan.

PMID: 31742414
DOI: 10.1021/acs.orglett.9b03990

Abstract

The synthesis of cis-β-amidevinyl benziodoxolones from the ethynyl benziodoxolone-chloroform complex and sulfonamides is reported. Evidence indicates that highly reactive unsubstituted ethynyl benziodoxolone undergoes Michael addition of sulfonamides, including sterically demanding acyclic amino acid derivatives. The synthesis of selectively deuterated cis-β-amidevinyl benziodoxolones and investigation of ethynyl-λ³-iodane reactivity are also described.

Publication types

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