Synthesis 2015; 47(09): 1245-1254
DOI: 10.1055/s-0034-1379901
paper
© Georg Thieme Verlag Stuttgart · New York

Concise Three-Step Strategy for the Synthesis of 2-Benzoxepin-3(1H)-ones

Hazra Madhurima
Indian Institute of Technology (IIT) Hyderabad, Ordnance Factory Estate Campus, Yeddumailaram – 502 205, Medak District, Telangana, India   Email: [email protected]
,
Jonnada Krishna
Indian Institute of Technology (IIT) Hyderabad, Ordnance Factory Estate Campus, Yeddumailaram – 502 205, Medak District, Telangana, India   Email: [email protected]
,
Gedu Satyanarayana*
Indian Institute of Technology (IIT) Hyderabad, Ordnance Factory Estate Campus, Yeddumailaram – 502 205, Medak District, Telangana, India   Email: [email protected]
› Author Affiliations
Further Information

Publication History

Received: 10 December 2014

Accepted after revision: 10 February 2015

Publication Date:
18 March 2015 (online)


Abstract

A short and efficient method was developed for the synthesis of 2-benzoxepin-3(1H)-ones. The synthetic sequence comprises of initial intermolecular Heck coupling, followed by reduction of the carbonyl functionality of the Heck product and finally base-induced intramolecular condensation. Notably, the final condensation may proceed by an interesting oxy-Michael addition, cycloreversion via double bond isomerization and intramolecular condensation.

Supporting Information

 
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