Syntheses of 2-Aroyl Benzofurans through Cascade Annulation on Arynes

Gouthami, Pashikanti ; Chavan, Lahu N. ; Chegondi, Rambabu ; Chandrasekhar, Srivari (2018) Syntheses of 2-Aroyl Benzofurans through Cascade Annulation on Arynes The Journal of Organic Chemistry, 83 (6). pp. 3325-3332. ISSN 0022-3263

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Official URL: http://doi.org/10.1021/acs.joc.8b00360

Related URL: http://dx.doi.org/10.1021/acs.joc.8b00360

Abstract

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.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society
ID Code:131295
Deposited On:06 Dec 2022 09:16
Last Modified:06 Dec 2022 09:16

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