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

Hazra Madhurima; Jonnada Krishna; Gedu Satyanarayana

doi:10.1055/s-0034-1379901

Synthesis, Table of Contents

Synthesis 2015; 47(09): 1245-1254
DOI: 10.1055/s-0034-1379901

paper

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: gvsatya@iith.ac.in

,

Jonnada Krishna

Indian Institute of Technology (IIT) Hyderabad, Ordnance Factory Estate Campus, Yeddumailaram – 502 205, Medak District, Telangana, India Email: gvsatya@iith.ac.in

,

Gedu Satyanarayana*

Indian Institute of Technology (IIT) Hyderabad, Ordnance Factory Estate Campus, Yeddumailaram – 502 205, Medak District, Telangana, India Email: gvsatya@iith.ac.in

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Abstract

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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.

Key words

palladium catalysis - Heck coupling - reduction - condensation - benzoxepinones

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References

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