Interaction of 3-pyridyland 3-(imidazo[1,2-a]pyridin-2-yl)isocoumarins with hydrazine

Authors

  • О.V. Shablykinа Taras Shevchenko National University of Kiev
  • O.F. Krekhovа Taras Shevchenko National University of Kiev
  • А.S. Konovalenkо V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the NAS of Ukraine, Kiev
  • V.S. Moskvinа Taras Shevchenko National University of Kiev
  • V.P. Khilyа Taras Shevchenko National University of Kiev

DOI:

https://doi.org/10.15407/dopovidi2018.12.071

Keywords:

3-hetaryl-1H-isochromen-1-ones, 3-hetaryl-N-amino-isoquinoline-1(2H)-ones, 3-hydrazinyl-3-hetarylisochroman-1-ones, 4-hetaryl-2;5-dihydro-1H-benzo[d][1;2]diazepine-1-ones, recyclization

Abstract

The products of 3-pyridyl- and 3-(imidazo[1,2-a]pyridin-2-yl)isocomarins' interaction with hydrazine are investigated. It has been shown that the recyclization of 1H-isochromen-1-one (isocoumarin) cycle to the 2,5-dihydro-1H-benzo[d][1,2]diazepine-1-one system occurs after the addition of a hydrazine molecule to the 3rd position of isocoumarin; and 4-hetaryl-2,5-dihydro-1H-benzo[d][1,2]diazepine-1-ones are recyclized into the corresponding 3-hetaryl-N-aminoisoquinoline-1(2H)-ones under acidic conditions.

Downloads

Download data is not yet available.

References

Walker, H. M. & Torres, P. A. (Eds.). (2014). Diazepam: medical uses, pharmacology and health effects. New York: Nova Science.

Ashton, H. (2005). The diagnosis and management of benzodiazepine dependence. Curr. Opin. Psychiatr., 18, No. 3, pp. 249-255. doi: https://doi.org/10.1097/01.yco.0000165594.60434.84

Bond, A. & Lader, M. (1982). A comparison of the psychotropic profiles of tofisopam and diazepam. Eur. J. Clin. Pharmacol., 22, No. 2, pp. 137-142. doi: https://doi.org/10.1007/BF00542458

Moskvina, V. S., Shablykina, O. V. & Khilya, V. P. (2017). Reactions of 3-Arylisocoumarins with N-Nucleophiles — A Route to Novel Azaheterocycles. Curr. Top. Med. Chem., 17, No. 29, pp. 3199-3212. doi: https://doi.org/10.2174/1568026618666171227124212

Kharaneko, O. I., Popov, V. Y. & Bogza, S. L. (2013). 4-Aryl-1-hydrazino-5H-2,3-benzodiazepine and 1-aryl-4-hydrazino-5H-2,3-benzodiazepine in the synthesis of condensed [1,2]diazepines. Chem. Heterocycl. Comp., 49, No. 2, pp. 317-324. doi: https://doi.org/10.1007/s10593-013-1249-6

Ishchenko, V. V., Shablykin, O. V., Turov, O. V., Shablykina, O. V. & Khilya, V. P. (2006). 3-Hetarylisocoumarins: synthesis and chemical properties. Dopov. Nac. akad. nauk. Ukr., No. 4, pp. 133-138 (in Ukrainian).

Le Bras, G., Hamze, A., Messaoudi, S., Provot, O., Le Calvez, P.-B., Brion, J.-D. & Alami, M. (2008). Synthesis of isocoumarin via PTSA-catalyzed annulation of diarylalkynes. Synthesis, No. 10, pp. 1607-1611. doi: https://doi.org/10.1055/s-2008-1072575

Shablykina, O. V., Shablykin, O. V., Ishchenko, V. V., Voronaya, A. V. & Khilya, V. P. (2013). Synthesis of 3-hetaryl-1H-isochromen-1-ones based on 3-(2-bromoacetyl)-1H-isochromen-1-one. Chem. Heterocycl. Compd., 48, No. 11, pp. 1621-1627. doi: https://doi.org/10.1007/s10593-013-1183-7

Konovalenko, A., Shablykina, O., Ishchenko, V. & Khilya, V. P. (2017). New 3-hetarylisocoumarins. Visn. KNU im. Tarasa Shevchenka. Khimiya, 53, No. 1, pp. 6-8 (in Ukrainian).

Downloads

Published

20.05.2024

How to Cite

Shablykinа О., Krekhovа O., Konovalenkо А., Moskvinа V., & Khilyа V. (2024). Interaction of 3-pyridyland 3-(imidazo[1,2-a]pyridin-2-yl)isocoumarins with hydrazine . Reports of the National Academy of Sciences of Ukraine, (12), 71–78. https://doi.org/10.15407/dopovidi2018.12.071

Issue

No. 12 (2018): Reports of the National Academy of Sciences of Ukraine

Section

Chemistry

License

Copyright (c) 2024 Reports of the National Academy of Sciences of Ukraine

Creative Commons License

This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.