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Paper | Regular issue | Vol 31, No. 11, 1990, pp.2011-2023
Published online, 1st January, 1970
DOI: 10.3987/COM-90-5540
Ring Opening 2-Acylamino-4,5-dihydro-3-furancarbonitriles by Use of Titanium (IV) Chloride

Hiroshi Maruoka, Kenji Yamagata, and Motoyoshi Yamazaki*

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

Abstract

The ring opening of 2-acylamino-4,5-dihydro-3-furanocarbonitriles (1a-f) with titanium (IV) chloride gave the corresponding N-acyl-4-chloro-2-cyanobutanamides (2a-f). On treatment with potassium carbonate, compounds (2a-f) were converted to the corresponding N-acyl-1-cyanocyclopropanecarboxamides (3a-f). On the other hand, the reaction of 2-benzamido-4,5-dihydro-3-thiophenecarbonitriles (4a-c) with titanium (IV) chloride gave the corresponding 2-benzamido-4,5-dihydro-3-thiophenecarboxamides (5a-c).