Syntheses of 2‑Aroyl Benzofurans through Cascade Annulation on Arynes

The highly efficient and expedient route for the syntheses of 2-aroyl benzofurans has been developed via the cascade [2+2] followed by a [4+1] annulation on arynes. The overall transformation proceeded through the formation of ortho-quinone methide by the insertion of transient aryne into N,N-dimeth...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2018-03, Vol.83 (6), p.3325-3332
Main Authors: Gouthami, Pashikanti, Chavan, Lahu N, Chegondi, Rambabu, Chandrasekhar, Srivari
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The highly efficient and expedient route for the syntheses of 2-aroyl benzofurans has been developed via the cascade [2+2] followed by a [4+1] annulation on arynes. The overall transformation proceeded through the formation of ortho-quinone methide by the insertion of transient aryne into N,N-dimethylformamide and subsequent trapping with sulfur ylide. Moreover, this transformation has a broad range of substrate scope with a high functional-group tolerance. This new reaction was successfully utilized in the synthesis of the potent CYP19 aromatase inhibitor and late-stage functionalization on the bioactive complex estrone.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b00360