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

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...

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Published inChemistry 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
LanguageEnglish
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
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Summary: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 substituents in the (het)aroyl moiety of (het)aroylpyruvate esters and the reaction conditions. The highest ratio of quinoxalinones relevant for medicinal chemistry was observed when using (het)aroylpyruvate esters without substituents that would cause a negative mesomeric effect in the (het)aroyl moiety, as well as when performing the reactions in acetic acid.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-023-03235-6