A NOVEL METHOD FOR THE SYNTHESIS OF PYRIDO[1,2-<i>b</i>][2]BENZAZEPINES ON THE BASIS OF 2-(BROMOMETHYL)BENZOPHENONES AND 2-(BROMOMETHYL)BENZALDEHYDE

Authors

  • Людмила М. Потиха Taras Shevchenko National University of Kyiv, 64 Volodymyrska St., Kyiv 01033, Ukraine
  • Владимир В. Сыпченко Taras Shevchenko National University of Kyiv, 64 Volodymyrska St., Kyiv 01033, Ukraine
  • Владимир А. Ковтуненко Киевский национальный университет им. Тараса Шевченко, ул. Владимирская, 64, Киев 01033, Украина

DOI:

https://doi.org/10.1007/5699

Keywords:

2-(bromomethyl)benzaldehyde, 2-(bromomethyl)benzophenone, 2-methylpyridine, pyrido[1, 2-b][2]benzazepine, vinylogy.

Abstract

A novel method for the synthesis of pyrido[1,2-b][2]benzazepine derivatives is based on the reaction of 2-(bromomethyl)benzophenones and 2-(bromomethyl)benzaldehyde with 2-methylpyridines. The route of synthesis of 6H-pyrido[1,2-b][2]benzazepinium salts includes several steps with the possibility of isolating intermediate 1-benzyl-2-methylpyridinium and 11-aryl-11-hydroxy-11,12-dihydro-6H-pyrido[1,2-b][2]benzazepinium bromides. The efficiency of dehydration of intermediate carbinols increases with the use of protic solvents, an increase in heating time, and in the presence of electron-withdrawing substituents in the benzazepine moiety. The structure
of the reaction products was proved by mass spectrometry, IR and one- and two-dimensional correlation NMR spectroscopy.

Author Biography

Людмила М. Потиха, Taras Shevchenko National University of Kyiv, 64 Volodymyrska St., Kyiv 01033, Ukraine

Кафедра органической химии, заведующая научно-исследовательской лабораторией

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Published

2020-11-26

Issue

Vol. 56 No. 11 (2020)

Section

Original Papers