Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
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
TAISEI UEDAISOO ITOYOICHI IITAKA
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1976 Volume 24 Issue 4 Pages 596-606

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Abstract
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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© The Pharmaceutical Society of Japan
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