Affiliation:
1. Institute of Chemistry Saint Petersburg State University 198504 Saint Petersburg Russia
Abstract
AbstractExclusive formation of 5‐aryl‐2‐trimethylsilyl‐4H‐pyran‐4‐ones is accomplished by a regioselective cyclization of 2‐aryl‐1‐ethoxy(hydroxy)‐5‐(trimethylsilyl)pent‐1‐en‐4‐yn‐3‐ones. This cyclization occurs in a 6‐endo‐dig mode through addition to the β‐atom of the TMS substituted triple bond. The reaction was found to be general for a range of ethoxyenynones upon heating in glacial acetic acid and for analogous hydroxyenynones in diphenyl ether. Plausible mechanistic explanation and possible post‐modifications of resulting pyranones are offered.
Funder
Russian Science Foundation
Subject
Organic Chemistry,Physical and Theoretical Chemistry