Formation of 4-(het)aryl-3H-1,5-benzodiazepine-2-carboxylates from (het)aroylpyruvate esters and o-phenylenediamine

• Published in: Chemistry of heterocyclic compounds (New York, N.Y. 1965) Vol. 59; no. 8; pp. 574 - 579
• Main Authors: Khramtsova, Ekaterina E., Dmitriev, Maksim V., Maslivets, Andrey N.
• Format: Journal Article
• Language: English
• Published: New York Springer US 01.08.2023; Springer Nature B.V
• Subjects: Acetic acid; Aromatic compounds; Benzodiazepines; Carboxylates; Chemistry; Chemistry and Materials Science; Esters; Organic Chemistry; Pharmacy; Phenylenediamine; pyruvic acids; 1,3-diketones; 1,5-benzodiazepines; phenylenediamine; cyclocondensation

Esters of (het)aroylpyruvic acids can react with o -phenylenediamine, leading to the formation of ( Z )-3-(2-(het)aryl-2-oxoethylidene)-3,4-dihydroquinoxalin-2(1 H )-ones and 4-(het)aryl-3 H -1,5-benzodiazepine-2-carboxylates. The obtained product ratio depends on the electronic effects due to subst...