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Short Paper | Special issue | Vol 88, No. 2, 2014, pp.1573-1579
Published online, 22nd August, 2013
DOI: 10.3987/COM-13-S(S)96
Preparation of New Heptafulvenes and the Related Compounds Derived from 2H-Cyclohepta[d]thiazol-2-one and -2-thione

Ohki Sato,* Nobuhiro Ando, and Tatsuro Toma

*Department of Chemistry, Graduate School of Science and Engineering, Saitama University, 255 Shimo-okubo, Sakura-ku, Saitama 338-8570 , Japan


2H-Cyclohepta[d]thiazol-2-one reacted with dimethyl malonate in the presence of sodium hydride to generate the 6- and 4-adducts, which were oxidized by DDQ to afford a 2-thiazolone-fuzed heptafulvene and a tricyclic compound, respectively. The reaction of 2H-cyclohepta[d]thiazol-2-thione under the same addition conditions gave the similar 6- and 4-adducts. Oxidation of each separated adducts afforded the corresponding regioisomeric heptafulvene disulfides with thiazole rings, respectively.