Sequential one-pot method for oxy-Michael addition, Heck coupling, and degradation followed by condensation: Facile synthesis of 2-benzoxepin-3(1H)

Reddy, A G K and Krishna, J and G, Satyanarayana (2013) Sequential one-pot method for oxy-Michael addition, Heck coupling, and degradation followed by condensation: Facile synthesis of 2-benzoxepin-3(1H). Tetrahedron, 69 (47). pp. 10098-10107. ISSN 0040-4020

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Abstract

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.

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IITH Creators:	IITH Creators ORCiD G, Satyanarayana UNSPECIFIED
Item Type:	Article
Uncontrolled Keywords:	2-Benzoxepin-3(1H)-ones; Condensation; Heck coupling; Oxy-Michael addition; Pd-catalysis; retro-Oxy-Michael addition
Subjects:	?? sub5.8 ??
Divisions:	Department of Chemistry
Depositing User:	Team Library
Date Deposited:	14 Nov 2014 10:40
Last Modified:	24 Sep 2015 10:24
URI:	http://raiithold.iith.ac.in/id/eprint/791
Publisher URL:	http://dx.doi.org/10.1016/j.tet.2013.09.050
OA policy:	http://www.sherpa.ac.uk/romeo/issn/0040-4020/
Related URLs:	Google Scholar

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