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Reactions of 2‐acyl‐1,3‐indandiones with monosubstituted hydrazines and hydrazides
Author(s) -
Mosher William A.,
Bechara Ibrahim S.
Publication year - 1970
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.5570070415
Subject(s) - chemistry , phenylhydrazine , yield (engineering) , acetic acid , medicinal chemistry , benzoic acid , organic chemistry , materials science , metallurgy
Methyl‐ and phenylhydrazines react with 2‐(diphenylacetyl)‐1,3‐indandione ( 1 ) to yield respectively the 1‐(methylhydrazone) and the 1‐(phenylhydrazone) of 2‐(diphenylacetyl)‐1,3‐indandione ( 2a and 2b ). In comparison, acetic and benzoic acid hydrazides react with 1 to give respectively the α‐(acetylhydrazone) and the α‐(benzoylhydrazone) of 2‐(diphenylacetyl)‐1,3‐indandione ( 3a and 3b ). Cyclization of 2a and 2b gives 2,3‐disubstituted indeno[1,2‐ c ]pyrazol‐4(2 H )‐ones ( 7a and 7b ). Cyclization of 3a and 3b , followed by methylation, gives 1‐methyl‐ and 2‐methyl‐3‐(diphenylmethyl)indeno[1,2‐ c ]pyrazol‐4(1 and 2 H )‐ones ( 9a and 9b ). 2‐Isovaleryl‐1,3‐indandione reacts with phenylhydrazine to give directly 3‐isobutyl‐1‐phenylindeno[1,2‐ c ]‐pyrazol‐4(1 H )‐one ( 10 ).