Synthesis of pyrazolone derivatives. XXVI. Reaction of 1-methyl-2-phenyl-1,2,3,10-tetrahydro-4H-benzo(6,7)thiepino(3,4-c)pyrazole-3,4-dione with dimethyl acetylenedicarboxylate.

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The Michael and the Diels-Alder reactions of 1-methyl-2-phenyl-1, 2, 3, 10-tetrahydro-4H-benzo [6, 7] thiepino [3, 4-c] pyrazole-3, 4-dione (1) with dimethyl acetylenedicarboxylate (2) were examined, and the fascinating reactions which gave two novel heterocycles were found : dimethyl 1, 2-dihydro-1-methyl-3-oxo-2-phenyl-3H-benzothieno [3, 2-e] indazole-9, 10-dicarboxylate (3) and dimethyl 1, 2-dihydro-4-hydroxy-1-methyl-3-oxo-2-phenyl-3H-[2] benzothiopyrano [4, 3, 2-f, g] indazole-8, 9-dicarboxylate (15). The mechanisms of the formations of 3 and 15 were discussed. For pharmacological evaluation some N, N-dimethylethylenediamine derivatives of 3 and 15 were synthesized.

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