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Paper | Regular issue | Vol 78, No. 1, 2009, pp.161-168
Published online, 18th September, 2008
DOI: 10.3987/COM-08-11509
One-Pot Synthesis of 1-Arylindole-3-carboxylates from 2-(2-Isocyanophenyl)acetates

Shuhei Fukamachi, Hisatoshi Konishi, and Kazuhiro Kobayashi*

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

Abstract

An efficient method for the preparation of 1-arylindole-3-carboxylates under mild conditions has been developed. Thus, cyclization of ethyl 2-(2-isocyanophenyl)acetates using sodium hydride at room temperature was followed by 1-arylation of the resulting ethyl 1-sodioindole-3-carboxylates with fluoro(di)nitrobenzenes to give ethyl 1-(di)nitrophenylindole-3-carboxylates in generally good yields. This method also allows preparation of 1,1’-(4,6-dinitro-1,3-phenylene)diindole derivatives by using 1,3-difluoro-4,6-dinitrobenzene.