Syntheses of 2-Aroyl Benzofurans through Cascade Annulation on Arynes

The Journal of Organic Chemistry
Pashikanti GouthamiSrivari Chandrasekhar

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.

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Citations

Apr 12, 2018·Organic & Biomolecular Chemistry·Kashmiri NeogPranjal Gogoi
May 18, 2018·Chemistry : a European Journal·Sébastien ClergueRaphaël Robiette
Feb 19, 2021·Chemical Reviews·Jiarong ShiYang Li
Jan 21, 2021·The Journal of Organic Chemistry·Abhilash SharmaPranjal Gogoi
May 4, 2021·Organic Letters·Karekar SanjeevSrivari Chandrasekhar
Aug 21, 2021·The Journal of Organic Chemistry·Shweta SinghGoverdhan Mehta

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