Gold-Catalyzed Heteroannulation of Anthranilic Acids with Alkynes: Synthesis of 3,1-Benzoxazin-4-ones.

J Org Chem

School of Pharmacy and Pharmaceutical Sciences, Mukogawa Women's University, 11-68, 9-Bancho, Koshien, Nishinomiya, Hyogo 663-8179, Japan.

Published: September 2024

We demonstrated a rapid and facile approach for the synthesis of various 3,1-benzoxazin-4-ones via a gold-catalyzed heteroannulation of readily available nonprotected anthranilic acids and simple aryl alkynes. Our preliminary mechanistic investigation indicated that the double incorporation of alkynes into anthranilic acids occurs through the formation of bisenamine intermediates.

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http://dx.doi.org/10.1021/acs.joc.4c01602DOI Listing

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