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Note | Regular issue | Vol 81, No. 6, 2010, pp.1467-1484
Published online, 16th April, 2010
DOI: 10.3987/COM-10-11936
Synthesis of Dihydroindoles and Tetrahydroquinolines by the Intramolecular Diels-Alder Reaction of N-Alkenylated 2-Acylamino-3-furancarbonitriles

Hiroshi Maruoka,* Fumi Okabe, Yoshimichi Koutake, Eiichi Masumoto, Toshihiro Fujioka, and Kenji Yamagata

*Faculty of Pharmaceutical Sciences, Fukuoka University, 8-19-1 Nanakuma, Jonan-ku, Fukuoka 814-0180, Japan

Abstract

An approach to dihydroindoles and tetrahydroquinolines from N-alkenylated 2-acylamino-3-furancarbonitriles via a [4 + 2] cycloaddition reaction is described. Thermal treatment of N-alkenylated 2-acylamino-3- furancarbonitriles 5ad, 6ad, 9ad, and 10ad, which were prepared from 2-acylamino-3-furancarbonitriles 3ad and/or 4ad and 4-bromo-1-butene and/or 5-bromo-1-pentene, caused an intramolecular Diels-Alder reaction to give the corresponding dihydroindole and tetrahydroquinoline derivatives 7ad, 8ad, 11ad, and 12ad. This method has the advantage of easier work-up procedure.