The unusual behaviour of substituted 1-aryl-2-(arylamino)ethanones towardsVilsmeier reagent

Authors
Majo, VJ Anand, RV Perumal, PT
Citation
Vj. Majo et al., The unusual behaviour of substituted 1-aryl-2-(arylamino)ethanones towardsVilsmeier reagent, I J CHEM B, 38(7), 1999, pp. 763-765
Citations number
26
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY
ISSN journal
03764699 → ACNP
Volume
38
Issue
7
Year of publication
1999
Pages
763 - 765
Database
ISI
SICI code
0376-4699(199907)38:7<763:TUBOS1>2.0.ZU;2-E
Abstract
An attempted synthesis of oxazolium salts from 1-aryl-2-(arylamino)ethanone s under VilsmeiEr conditions results in the formation of 1-aryl-2-(N-formyl -N-arylamino)ethanones 4 as the major product. Vinyl chlorides are obtained in low yield by the reaction of carbonyl group only in a few cases. The pr oposed reaction mechanism involves the formation of an intermediate cyclic oxazolidine derivative which accounts for the low reactivity of carbonyl gr oup and lack of formation of N-formylvinyl chloride.