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Paper | Regular issue | Vol 81, No. 3, 2010, pp.675-688
Published online, 28th January, 2010
DOI: 10.3987/COM-09-11894
Synthesis of Fused Thiopyranthione and Thiophene Derivatives from 4,5-Dihydro-3-thiophene(and -3-furan)carbonitriles Having an Active Methylene Group at C-2 Position

Hiroshi Maruoka,* Fumi Okabe, Keishi Yamasaki, Eiichi Masumoto, Toshihiro Fujioka, and Kenji Yamagata

*Faculty of Pharmaceutical Sciences, Fukuoka University, 8-19-1 Nanakuma, Jonan-ku, Fukuoka 814-0180, Japan


A versatile strategy is described for the synthesis of new fused thiopyranthione and thiophene derivatives. The reaction of heterocyclic α,β-unsaturated nitriles 3ac, 4ad, 5ac, and 6ad, which were prepared from tetrahydro-2-oxo-3-thiophene- and -3-furan-carbonitriles 1ac and/or 2ad and alkylidene phosphoranes such as (triphenylphosphoranylidene)acetonitrile and methyl (triphenylphosphoranylidene)acetate through Wittig reaction, with carbon disulfide in the presence of sodium hydride in THF gave the corresponding 6-thioxothieno[3,2-c]thiopyran and 6-thioxothiopyrano[4,3-b]furan derivatives 7ac, 8ad, 9ac, and 10ad. On the other hand, treatment of compounds 3ac, 5ac, and 6ad with sulfur powder in the presence of triethylamine in methanol caused Gewald reaction to provide the corresponding thieno[3,4-b]thiophene and -furan derivatives 11ac, 12ac, and 13ad.