Iodo- and Chalcogenoannulation of Morita-Baylis-Hillman Alcohols of Propiolaldehydes: Entry to Functionalized 2-Pyrones

Chada Raji Reddy* and Amol D. Patil

*Department of Organic Synthesis & Process Chemistry, CSIR−Indian Institute of Chemical Technology, Hyderabad 500007, India, Email: rajireddyiict.res.in

C. R. Reddy, A. D. Patil, Org. Lett., 2021, 23, 4749-4753.

DOI: 10.1021/acs.orglett.1c01466

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Abstract

An efficient intramolecular annulation of Morita-Baylis-Hillman (MBH) alcohols of propiolaldehydes in the presence of ICl or PhSeSePh/PhSSPh-CuCl₂ provides a wide variety of iodinated or chalcogenated 3-(chloromethyl)-2-pyrones in good yields. The chloromethyl group can easily be converted to other functionalities.

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proposed mechanism

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Key Words

2-Pyrones

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ID: J54-Y2021