FORMATION OF 4-(HET)ARYL-3<i>H</i>-1,5-BENZODIAZEPINE-2-CARBOXYLATES FROM (HET)AROYLPYRUVATE ESTERS AND <i>o</i>-PHENYLENEDIAMINE

Authors

  • Екатерина Е. Храмцова Perm State University, 15 Bukireva St., Perm 614990, Russia
  • Максим В. Дмитриев Perm State University, 15 Bukireva St., Perm 614990, Russia
  • Андрей Н. Масливец Perm State University, 15 Bukireva St., Perm 614990, Russia

DOI:

https://doi.org/10.1007/7252

Keywords:

1, 5-benzodiazepines, 3-diketones, о-phenylenediamine, pyruvic acids, cyclocondensation.

Abstract

Esters of (het)aroylpyruvic acids can react with о-phenylenediamine, leading to the formation of (Z)-3-(2-(het)aryl-2-oxoethylidene)-3,4dihydroquinoxalin-2(1H)-ones and 4-(het)aryl-3H-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.

 

Author Biographies

Екатерина Е. Храмцова, Perm State University, 15 Bukireva St., Perm 614990, Russia

доцент кафедрой органической химии

Максим В. Дмитриев, Perm State University, 15 Bukireva St., Perm 614990, Russia

доцент кафедрой органической химии

Андрей Н. Масливец, Perm State University, 15 Bukireva St., Perm 614990, Russia

заведующий кафедрой органической химии

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Published

2023-09-04

Issue

Vol. 59 No. 8 (2023)

Section

Original Papers