6533b839fe1ef96bd12a598c

RESEARCH PRODUCT

Cyclocondensation reaction of 1,2-diamino-4-methylbenzene andp-substituted acetophenones

Rodrigo AboniaHerbert MeierJairo QuirogaBraulio Insuasty

subject

chemistry.chemical_classificationKetoneBicyclic moleculeOrganic ChemistrySulfuric acidNuclear magnetic resonance spectroscopyCondensation reactionMedicinal chemistrychemistry.chemical_compoundchemistryDiamineStructural isomerOrganic chemistryAcetophenone

description

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-1H-1,5-benzodiazepines 3a-e and as minor component 2,4-diaryl-2,3-dihydro-2,7-dimethyl-1H-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.

yearjournalcountryeditionlanguage
1993-01-01Journal of Heterocyclic Chemistry
https://doi.org/10.1002/jhet.5570300139