A sequential one-pot intermolecular oxy-Michael addition, intermolecular Heck coupling, and intramolecular degradation (retro-oxy-Michael addition) followed by condensation method has been developed for the synthesis of interesting 2-benzoxepin-3(1H)-ones. Significantly, the 2-benzoxepin-3(1H)-ones form the core quantum of biologically vital natural products. The initial oxy-Michael addition and Heck coupling steps involve a straight forward construction of C-O and C-C bonds, whereas, the final condensation step follows a novel mechanistic path via intramolecular degradation, double bond isomerization, and intramolecular condensation. Notably, a remarkable solvent effect has been observed in-order to promote the final intramolecular condensation. © 2013 Elsevier Ltd. All rights reserved.

Satyanarayana Gedu

Department of Chemistry

A.G.K. Reddy

J. Krishna

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IIT Hyderabad

Tetrahedron

Sequential one-pot method for oxy-Michael addition, Heck coupling, and degradation followed by condensation: Facile synthesis of 2-benzoxepin-3(1H)- ones Dedicated to the memory of my teacher Professor P.V. Subba Rao, Department of Chemistry, Andhra University, Visakhapatnam

Journal	Tetrahedron
ISSN	00404020