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Paper | Regular issue | Vol 92, No. 6, 2016, pp.1063-1074
Published online, 8th April, 2016
DOI: 10.3987/COM-16-13450
Synthesis of 1-Aroyl-1,2-dihydro-3H-indol-3-ones via Cyclization of N-[2-(2-Chloroacetyl)phenyl]benzamides with Triethylamine in the Presence of Di-tert-butyl Dicarbonate

Kazuhiro Kobayashi,* Daiki Kado, and Kohei Nishikawa

*Division of Applied Chemistry, Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan

Abstract

1-Aroyl-1,2-dihydro-3H-indol-3-ones can now be conveniently obtained from 2-aryl-4-(Z)-(chloromethylidene)-4H-3,1-benzoxazines using an easy operated three-step sequence under mild conditions. Thus, the starting materials are hydrolyzed with dilute hydrochloric acid at 0 ˚C to N-[2-(2-chloroacetyl)phenyl]benzamides, of which treatment with triethylamine in the presence of di-tert-butyl dicarbonate at room temperature, followed by deprotection with trifluoroacetic acid at room temperature, provides the desired products.