THE INTERACTION OF 6-SUBSTITUTED 4-PYRONE-2-CARBOXYLIC ACIDS WITH <i>o</i>-PHENYLENEDIAMINE. SYNTHESIS AND STRUCTURE OF 3-(1<i>H</i>-1,5-BENZODIAZEPIN-2(3<i>Н</i>)-YLIDENEMETHYL)QUINOXALIN-2(1<i>H</i>)-ONES

Authors

  • Дмитрий Л. Обыденнов Institute of Natural Sciences, Ural Federal University, 51 Lenina Ave., Yekaterinburg 620000, Russia
  • Вячеслав Я. Сосновских Institute of Natural Sciences, Ural Federal University, 51 Lenina Ave., Yekaterinburg 620000, Russia

DOI:

https://doi.org/10.1007/2215

Keywords:

1, 5-benzodiazepines, comanic acids, о-phenylenediamine, 4-pyrones, quinoxalin-2-ones, tautomerism

Abstract

6-Aryl(alkyl)-4-pyrone-2-carboxylic acids upon refluxing in n-BuOH react with two equivalents of о-phenylenediamine, giving 26–85% yields of 3-(1H-1,5-benzodiazepin-2(3H)-ylidenemethyl)quinoxalin-2(1H)-ones, which exist in two tautomeric forms. The direction of the initial nucleophilic attack on the pyrone ring and the tautomeric composition of the obtained products is mainly determined by the substituent at the С-6 atom. Quantum-chemical calculations were used to estimate the stability of tautomers in the gas phase.

How to Cite
Obydennov, D. L.; Sosnovskikh, V. Y. Chem. Heterocycl. Compd. 2015, 51, 281. [Khim. Geterotsikl. Soedin. 2015, 51, 281.]

For this article in the English edition see DOI 10.1007/s10593-015-1696-3

Author Biographies

Дмитрий Л. Обыденнов, Institute of Natural Sciences, Ural Federal University, 51 Lenina Ave., Yekaterinburg 620000, Russia

Дмитрий Львович Обыденнов

доцент кафедры органической химии ИЕН УРФУ

Вячеслав Я. Сосновских, Institute of Natural Sciences, Ural Federal University, 51 Lenina Ave., Yekaterinburg 620000, Russia

Вячеслав Яковлевич Сосновских

заведующий кафедры органической химии ИЕН УРФУ

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Published

2015-03-18

Issue

Vol. 51 No. 3 (2015)

Section

Original Papers