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...

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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
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cited_by cdi_FETCH-LOGICAL-a366t-28f1be829f61ed545c990ca5804cb7463fc1150976b6a7c2ea593dd9480490823
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creator Gouthami, Pashikanti
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description 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.
doi_str_mv 10.1021/acs.joc.8b00360
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title Syntheses of 2‑Aroyl Benzofurans through Cascade Annulation on Arynes
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