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Studies on the synthesis of heterocyclic compounds. III. Preparation of some pyrazolo[3,4‐ C ] [1,5]benzodiazocin‐10(11 H )one derivatives
Author(s) -
Plescia Salvatore,
Daidone Guiseppe,
Sprio Vincenzo
Publication year - 1979
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570160521
Subject(s) - chemistry , benzamide , yield (engineering) , derivative (finance) , medicinal chemistry , phosphorus , stereochemistry , organic chemistry , materials science , economics , financial economics , metallurgy
Starting from the readly available N ‐melhyl‐ N ‐(1‐phenyl‐3‐R‐pyrazol‐5‐yl)‐2‐nitrobenzamides (1a,b), the pyrazoles, 4‐aeetyl substituted 2a,b, were prepared in high yield. Reduction of 2a gave the amino derivative 4a, which was eyclized to the desired pyrazolo[3,4‐ c ][1,5]benzodiazo‐cin‐10(11 H )one (5a). Compound 2b afforded 5b directly. Compound 5b was also prepared by the action of phosphorus oxychloride on N ‐methyl‐ N ‐(1,3‐diphenylpyrazol‐5‐yl)‐2‐acetamido‐benzamide (6b).