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Short Paper | Regular issue | Vol 89, No. 4, 2014, pp.1025-1034
Published online, 7th February, 2014
DOI: 10.3987/COM-14-12931
An Efficient Synthetic Route towards Novel Furo- and Thieno-triazolopyridines

Kazuhiro Tomoike, Hiroshi Maruoka,* Fumi Okabe, 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 efficient method for the synthesis of novel nitrogen-containing heterotricycles is described. 4,5-Dihydro-3-furan- and -3-thiophene-carbonitriles 1a,b and 2a,b having an active methylene group at C-2 position served as the precursor of enamines 3a,b and 4a,b, which were followed by an exchange reaction of amines, such as acetohydrazide and benzohydrazide, and subsequent tandem intramolecular cyclization reaction to lead the corresponding furo- and thieno-triazolopyridines 5a,b, 6a,b, 7a,b, and 8a,b.