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Communication | Regular issue | Vol 4, No. 4, 1976, pp.705-712
Published online, 1st January, 1970
DOI: 10.3987/R-1976-04-0705
Cycloaddition Extrusion Reaction of 2- or 4-(Methylthio)thiocarbonylimino-1,2 or 1,4-Dihydropyridine Derivatives with Dimethyl Acetylenedicarboxylate

Kazumichi Mizuyama, Yoshinori Tominaga, Yoshiro Matsuda, and Goro Kobayashi*

*Faculty of Pharmaceutical Sciences, Nagasaki University, 1-14, Bunkyo-machi, Nagasaki 852-8521, Japan


Reaction of (methylthio)thiocarbonylimino derivatives of pyridine (Ia-d, IV) with dimethyl acetylenedicarboxylate (DMAD) afforded 2 or 4-(1,2-dimethoxycarbonyl-2-thioxoethy1idene)-1,2 or 1,4-dihydropyridine derivatives (IIa-d, V), accompanied with extrusion of methyl thiocyanate1) from 1,4-cycloadduct, spiro-1,3-thiazine derivatives.
Further, reaction of IV with DMAD (2 mole) gave cyclobuteno[l,2-b]azocine derivative (VI). Reaction of (methylthio)thiocarbonylimino derivative of benzothiazole (VII) with DMAD afforded 4H-pyrrole-2-spiro-2-(2,3-dihydrobenzothiazole) (VIII), accompanied with desulfrization.