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Communication | Special issue | Vol 70, No. 1, 2006, pp.93-99
Published online, 26th September, 2006
DOI: 10.3987/COM-06-S(W)26
Diastereoselective Synthesis of Atropisomeric 3-(2-Substituted Aryl)quinazolin-4-ones and Their Stereochemical Properties

Takashi Tokitoh, Toshitake Kobayashi, Eisuke Nakada, Tohru Inoue, Satoshi Yokoshima, Hideyo Takahashi, and Hideaki Natsugari*

*Faculty of Pharmaceutical Sciences, Teikyo University, 1091-1 Suarashi, Sagamiko-machi, Tsukui-gun, Kanagawa 199-0195, Japan


Atropisomeric {1-[(2-substituted-aryl)-4-oxo-3,4-dihydroquinazolin-2-yl]ethyl and -2-phenylethyl}carbamic acid t-butyl ester (9a-c) were diastereoselectively synthesized by acid-catalyzed cyclization of {2-[(2-substituted-arylcarbamoyl)phenylimino]-1-methyl- and -1-benzyl-2-piperidin-1-yl}carbamic acid t-butyl ester (8a-c). Investigation of the stereochemical properties of 9 revealed that both atropisomers have high stereochemical stability and the (aR*, S*)-form (9R*) is stereochemically more stable than the isomeric (aS*, S*)-form (9S*).