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Paper | Special issue | Vol 79, No. 1, 2009, pp.609-616
Published online, 1st December, 2008
DOI: 10.3987/COM-08-S(D)24
Synthesis of Aza-Bridged Calix(4-methoxy)triazines toward Flattened π-Conjugated Macrocycles

Hiroyuki Tanaka, Ayako Wada, Motoo Shiro, Kazuhito Hioki, Daiki Morisaki, and Munetaka Kunishima*

*Faculty of Pharmaceutical Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa, Ishikawa 920-1192, Japan

Abstract

Calixtriazines containing a 4-alkoxy-1,3,5-triazine backbone were efficiently synthesized by sequential fragment coupling started from 4-alkoxy-2,6-dichrolo-1,3,5-triazine. These macrocycles tend to form flattened conformations, leading to a stable π-conjugated system, presumably due to the electronic features of the alkoxy-substituent on the triazine rings.