A REACTION OF BERBERINE WITH AMIDES IN ALKALINE MEDIA: AN EXPERIMENTAL AND QUANTUM CHEMICAL STUDY

Authors

  • Александр Д. Загребаев Department of Chemistry, Southern Federal University, 7 Zorge St., Rostov-on-Don 344090, Russia
  • Олег Н. Буров Department of Chemistry, Southern Federal University, 7 Zorge St., Rostov-on-Don 344090, Russia
  • Михаил Е. Клецкий Department of Chemistry, Southern Federal University, 7 Zorge St., Rostov-on-Don 344090, Russia
  • Сергей В. Курбатов Department of Chemistry, Southern Federal University, 7 Zorge St., Rostov-on-Don 344090, Russia

DOI:

https://doi.org/10.1007/6681

Keywords:

berberine, dihydroberberine, nucleophilic substitution, N-nucleophiles, DFT calculations.

Abstract

The possibility of obtaining electroneutral 8-amido derivatives of dihydroberberines was shown experimentally and with the support of quantum chemical calculations based on the density functional theory (B3LYP/6-311+G(d,p)). In alkaline media, amides deprotonated to form amide anions, which, in turn, could add to the berberine framework at the C-8 position. Competing processes in this case were the reactions of the formation of 8-hydroxy- or 8-alkoxyberberines.

 

Author Biographies

Александр Д. Загребаев, Department of Chemistry, Southern Federal University, 7 Zorge St., Rostov-on-Don 344090, Russia

Младший научных сотрудник кафедры химии природных и высокомолекулярных соединений химического факульткта ЮФУ

Олег Н. Буров, Department of Chemistry, Southern Federal University, 7 Zorge St., Rostov-on-Don 344090, Russia

Доцент кафедры химии природных и высокомолекулярных соединений химического факульткта ЮФУ

Михаил Е. Клецкий, Department of Chemistry, Southern Federal University, 7 Zorge St., Rostov-on-Don 344090, Russia

Доцент кафедры химии природных и высокомолекулярных соединений химического факульткта ЮФУ

Сергей В. Курбатов, Department of Chemistry, Southern Federal University, 7 Zorge St., Rostov-on-Don 344090, Russia

Заведующий кафедрой химии природных и высокомолекулярных соединений химического факульткта ЮФУ

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Published

2022-07-21

Issue

Vol. 58 No. 6/7 (2022)

Section

Short Communications