Tandem migration-carboalkoxylation of o-isocyanophenyl acetals leading to benzoxazoles

Takashi Okitsu; Kenta Nagase; Nobuhiko Nishio; Akimori Wada

doi:10.1021/ol203175a

Tandem migration-carboalkoxylation of o-isocyanophenyl acetals leading to benzoxazoles

Org Lett. 2012 Feb 3;14(3):708-11. doi: 10.1021/ol203175a. Epub 2012 Jan 17.

Authors

Takashi Okitsu¹, Kenta Nagase, Nobuhiko Nishio, Akimori Wada

Affiliation

¹ Department of Organic Chemistry for Life Science, Kobe Pharmaceutical University, 4-19-1, Motoyamakita-machi, Kobe 658-8558, Japan.

PMID: 22251100
DOI: 10.1021/ol203175a

Abstract

An efficient approach to benzoxazoles via tandem migration-carboalkoxylation of o-isocyanophenyl acetals has been developed. Both a Lewis acid and base are essential for this reaction, and the BF(3)·OEt(2)/2,4,6-collidine combination is the best choice for cooperative transformation.

Publication types

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

MeSH terms

Acetals / chemistry*
Alcohols / chemistry*
Benzoxazoles / chemical synthesis*
Cyanides / chemistry*
Molecular Structure

Substances

Acetals
Alcohols
Benzoxazoles
Cyanides
alkoxyl radical