Ipso-cyclization via a dienone-phenol rearrangement of alkynyloxy cyclohexadienones for the synthesis of oxaspiro[4.5]trienones

TitleIpso-cyclization via a dienone-phenol rearrangement of alkynyloxy cyclohexadienones for the synthesis of oxaspiro[4.5]trienones
Publication TypeJournal Article
Year of Publication2025
AuthorsRai, A, Kundu, AI, Shukla, E, Das, U
JournalJournal of Organic Chemistry
Volume90
Issue38
Pagination13399-13406
Date PublishedSEP
Type of ArticleArticle
ISSN0022-3263
Abstract

Herein, we present a convenient method to access oxaspiro[4.5]trienone compounds from alkynyloxy cyclohexadienones. The reactions are catalyzed by Lewis/Bronsted acids, yielding the desired products in moderate to good yields under very mild reaction conditions. The process, which involves a dienone-phenol rearrangement, is characterized by its simplicity and the absence of any additional activators. The synthesis of the oxaspiro[4.5]trienone compounds is amenable to gram-scale reactions along with subsequent product transformations, making this approach practical and attractive.

DOI10.1021/acs.joc.5c00893
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

3.3

Divison category: 
Organic Chemistry
Database: 
Web of Science (WoS)

Add new comment