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Paper | Special issue | Vol 73, No. 1, 2007, pp.325-339
Published online, 5th June, 2007
DOI: 10.3987/COM-07-S(U)6
Syntheses of 2-Formyl-, 2,3-Diformyl- and 8-Formyl-1-azaazulenes

Kazuya Koizumi, Chikara Miyake, Tomoyuki Ariyoshi, Kenji Umeda, Noriko Yamauchi, Shoji Tagashira,* Yoshiko Murakami, Hiroyuki Fujii, and Noritaka Abe*

*Applied Molecular Bioscience, Graduate School of Medicine, and Department of Biology and Chemistry, Faculty of Science, Yamaguchi University, Yoshida, Yamaguchi 753-8512, Japan

Abstract

2-Styryl-1-azaazulenes were synthesized by two ways: a) Suzuki coupling of 2-bromo-1-azaazulenes with trans-2-phenylvinylboronic acid b) Condensation of 2-methyl-1-azaazulene, being synthesized by Negishi coupling of 2-bromo-1-azaazulene with dimethylzinc, with benzaldehyde. Oxidative cleavage of 2-styryl-1-azaazulenes with OsO4-KIO4 gave 2-formyl-1- azaazulenes. 8-Formyl-1-azaazulenes were synthesized by the reaction of 1- azaazulenes with 2-lithio-1,3-dithiane followed by the hydrolysis.