One-pot transition-metal-free synthesis of dibenzo[b,f]oxepins from 2-halobenzaldehydes

Young Lok Choi; Hye Sun Lim; Hwan Jung Lim; Jung-Nyoung Heo

doi:10.1021/ol302371s

One-pot transition-metal-free synthesis of dibenzo[b,f]oxepins from 2-halobenzaldehydes

Org Lett. 2012 Oct 5;14(19):5102-5. doi: 10.1021/ol302371s. Epub 2012 Sep 17.

Authors

Young Lok Choi¹, Hye Sun Lim, Hwan Jung Lim, Jung-Nyoung Heo

Affiliation

¹ Medicinal Chemistry Research Center, Korea Research Institute of Chemical Technology, 141 Gajeong-ro, Daejeon 305-600, Korea.

PMID: 22984846
DOI: 10.1021/ol302371s

Abstract

A one-pot transition-metal-free, base-mediated synthesis of dibenzo[b,f]oxepins was developed. The reaction of 2-halobenzaldehydes with (2-hydroxyphenyl)acetonitriles proceeds via a sequential aldol condensation and intramolecular ether formation reaction in the presence of Cs(2)CO(3) and molecular sieves in toluene.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Benzaldehydes / chemistry*
Benzene / chemistry*
Isomerism
Models, Molecular
Molecular Structure
Oxepins / chemical synthesis*

Substances

Benzaldehydes
Oxepins
Benzene
benzaldehyde