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Communication | Regular issue | Vol 20, No. 7, 1983, pp.1263-1266
Published online, 1st January, 1970
DOI: 10.3987/R-1983-07-1263
The Synthesis and Several Reactions of 2-Methylazuleno[2,1-d]thiazole

Kameji Yamane, Kunihide Fujimori, Shuji Ichikawa, Shiro Miyoshi, and Kenichi Hashizume

*Department of Chemistry, Faculty of Science, Shinshu University, Asahi, Matsumoto 390-8621, Japan

Abstract

2-Methylazuleno[2,1-d]thiazole was synthesized from 2-amino, 2-formylamino, and 2-acetylamino derivatives of ethyl azulene-1-carboxylate in four steps. The 9-dimethylaminomethyl, 9-piperidinomethyl, and 9-morpholinomethyl derivatives were prepared by Mannich reaction of 2-methylazuleno[2,1-d]thiazole. The Vilsmeyer-Haack reaction of 2-methylazuleno[2,1-d]thiazole gave the 9-formyl derivative, and dehydration of its oxime afforded the 9-cyano derivative.