Cyclization of N-Arylacrylamides via Radical Arylsulfenylation of Carbon-Carbon Double Bonds with Sulfonyl Hydrazides.
J Org Chem
; 80(24): 12697-703, 2015 Dec 18.
Article
em En
| MEDLINE
| ID: mdl-26583837
ABSTRACT
An unprecedented tandem radical sulfenylation/cyclization reaction of N-arylacrylamides with sulfonyl hydrazides has been developed in the presence of iodine for the selective synthesis of 3-(sulfenylmethyl)oxindoles and 3-sulfenyl-3,4-dihydroquinolin-2(1H)-ones. Preliminary mechanistic studies showed that sulfonyl hydrazides decomposed completely at an early stage to thiosulfonates and disulfides, both of which underwent tandem radical sulfenylation/cyclization with N-arylacrylamides at a late stage.
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Coleções:
01-internacional
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MEDLINE
Idioma:
En
Ano de publicação:
2015
Tipo de documento:
Article