UNEXPECTED TRANSFORMATION OF 1,5-BENZODIAZEPINE DERIVATIVES UNDER IMIDAZO-ANNULATION REACTION CONDITIONS

Authors

  • Mantas Jonušis Vilnius University, Life Sciences Centre, Institute of Biochemistry, 12A Mokslininkų St., Vilnius LT-08412, Lithuania
  • Aušra Vektarienė Vilnius University, Institute of Theoretical Physics and Astronomy, 3 Saulėtekio St., Vilnius LT-10257, Lithuania
  • Gema Mikulskienė Vilnius University, Life Sciences Centre, Institute of Biochemistry, 12A Mokslininkų St., Vilnius LT-08412, Lithuania
  • Simona Jonušienė Vilnius University, Life Sciences Centre, Institute of Biochemistry, 12A Mokslininkų St., Vilnius LT-08412, Lithuania
  • Dalia Vektarytė Vilnius University, Life Sciences Centre, 7 Saulėtekio St., Vilnius LT-10257, Lithuania
  • Regina Jančienė Vilnius University, Life Sciences Centre, Institute of Biochemistry, 12A Mokslininkų St., Vilnius LT-08412, Lithuania

DOI:

https://doi.org/10.1007/6781

Keywords:

1, 5-benzodiazepin-2-one, oxazole, computational molecular modeling, imidazo-annulation, NMR analysis.

Abstract

In an attempt to synthesize new derivatives of imidazo[1,5-a][1,5]benzodiazepine-3-carboxylic acid esters by activation of the amide group of the heterocycle to iminophosphate and its cyclocondensation with ethyl isocyanoacetate, unexpected 5-substituted ethyl oxazole-4-carboxylates were obtained as the main products. Structures of the novel oxazole derivatives were confirmed by IR, 1H, 13C, and 31P NMR, and mass spectra, and the reaction course was rationalized using computational molecular modeling techniques.

 

Author Biography

Mantas Jonušis, Vilnius University, Life Sciences Centre, Institute of Biochemistry, 12A Mokslininkų St., Vilnius LT-08412, Lithuania

Dr. Mantas Jonušis

VU LSC Institute of Biochemistry

Mokslininku 12A, LT-08412 Vilnius, LITHUANIA

Tel: +370 61601747

alternative e-mail: mantas.jonusis@gmail.com

Downloads

Published

2023-05-31

Issue

Vol. 59 No. 4/5 (2023)

Section

Original Papers