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

1Shablykina, OV
Krekhova, OF
Konovalenko, AS
1Moskvina, VS
1Khilya, VP
1Taras Shevchenko National University of Kyiv
Dopov. Nac. akad. nauk Ukr. 2018, 12:71-78
Section: Chemistry
Language: Ukrainian

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.

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
  1. Walker, H. M. & Torres, P. A. (Eds.). (2014). Diazepam: medical uses, pharmacology and health effects. New York: Nova Science.
  2. Ashton, H. (2005). The diagnosis and management of benzodiazepine dependence. Curr. Opin. Psychiatr., 18, No. 3, pp. 249-255. doi:
  3. 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:
  4. 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:
  5. 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:
  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).
  7. 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:
  8. 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:
  9. 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).