Construction of Naphtho[2,1-]oxazoles and 1,4-Epoxyisoquinolines via Regioselectivity-Switchable Diels-Alder Reaction of 4-Alkenyloxazoles with Arynes.

J Org Chem

Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry & Molecular Engineering, East China University of Science and Technology, Shanghai 200237, P. R. China.

Published: December 2024

A Regioselectivity-switchable Diels-Alder reaction of arynes and 4-alkenyloxazoles was explored. By regulating the reaction temperature and the polarity of the solvent, the reaction activity of aryne was controlled to selectively react with different favorable reaction sites of 4-alkenyloxazoles, providing naphtho[2,1-]oxazoles and 1,4-epoxyisoquinolines. Density functional theory (DFT) calculations demonstrated that the Diels-Alder reaction on acyclic dienes site needs more energy than the reaction on cyclic dienes to overcome the potential reaction barrier.

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http://dx.doi.org/10.1021/acs.joc.4c01919DOI Listing

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