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Paper | Special issue | Vol 82, No. 2, 2010, pp.1283-1296
Published online, 6th August, 2010
DOI: 10.3987/COM-10-S(E)74
2-[1,3-Bis(ethoxycarbonyl)azulen-6-yl]ethynyltriphenylphosphonium Bromide

Noboru Morita,* Shiro Moriyama, Kozo Toyota, Masataka Watanabe, Shigeru Kikuchi, Shunji Ito, and Kunihide Fujimori

*Department of Chemistry, Graduate School of Science, Tohoku University, Aoba-ku, Sendai 980-8578, Japan

Abstract

2-[1,3-Bis(ethoxycarbonyl)azulen-6-yl]ethynyltriphenylphosphonium bromide was prepared from diethyl 6-ethynyl-1,3-azulenedicarboxylate. Its NMR spectroscopic property was made clear. Furthermore, its reactivity with o-substituted aniline was studied, comparing with 1- and 2-ethynyl azulene derivatives. We found that 2-[3-(methoxycarbonyl)azulen-1-yl]ethynyltriphenyl- phosphonium bromide also reacted with o-substituted anilines in CHCl3 to give corresponding 2-[1,3-bis(ethoxycarbonyl)azulen-6-yl]benzoazoles. However, in DMSO another products were obtained.