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Cyclocondensation reaction of 1,2‐diamino‐4‐methylbenzene and p ‐substituted acetophenones
Author(s) -
Insuasty Braulio,
Abonia Rodrigo,
Quiroga Jairo,
Meier Herbert
Publication year - 1993
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.5570300139
Subject(s) - chemistry , structural isomer , medicinal chemistry , stereochemistry
1,2‐Diamino‐4‐methylbenzene 1 reacts in the presence of sulphuric acid with 4‐substituted acetophenones 2a‐e yielding 2,4‐diaryl‐2,3‐dihydro‐2,8‐dimethyl‐1 H ‐1,5‐benzodiazepines 3a‐e and as minor component 2,4‐diaryl‐2,3‐dihydro‐2,7‐dimethyl‐1 H ‐1,5‐benzodiazepines 4a‐e . The ratio 3:4 is in the range of 7:3. The structure determination of the regioisomers was performed by NOE measurements.
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