Base-free and catalyst-free synthesis of functionalized dihydrobenzoxazoles via vinylogous carbonate to carbamate rearrangement

TitleBase-free and catalyst-free synthesis of functionalized dihydrobenzoxazoles via vinylogous carbonate to carbamate rearrangement
Publication TypeJournal Article
Year of Publication2017
AuthorsDas, TKanti, Mondal, S, Gonnade, RG, Biju, AT
JournalOrganic Letters
Volume19
Date PublishedOCT
Type of ArticleArticle
Abstract

An unexpected, catalyst-free, and base-free intramolecular cyclization of N-aryloxyacrylate aldimines, under thermal conditions leading to the synthesis of functionalized dihydrobenzoxazoles, is reported. The reaction features a unique rearrangement of vinylogous carbonates to vinylogous carbamates resulting in a new carbon–oxygen and carbon–nitrogen bond construction. The reaction tolerates a broad range of functional groups and the desired products are formed in moderate to good yields.

DOI10.1021/acs.orglett.7b02733
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

6.732

Divison category: 
Center for Material Characterization (CMC)
Organic Chemistry