SYNTHESIS OF 5-AMINO-1<i>H</i>-PYRAZOLO[4,3-<i>b</i>]PYRIDINE DERIVATIVES AND ANNULATION OF IMIDAZOLE AND PYRIMIDINE RINGS THERETO

Authors

  • Георгий Г. Яковенко National University ''Kyiv-Mohyla Academy'', 2 Hrygorija Skorovody St., Kyiv 04655, Ukraine Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., Kyiv 02660, Ukraine
  • Олег А. Лукьянов Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., Kyiv 02660, Ukraine
  • Марта С. Ягодкина-Яковенко Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., Kyiv 02660, Ukraine
  • Андрей В. Больбут Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., Kyiv 02660, Ukraine Enamine Ltd., 78 Chervonotkatska St., Kyiv 02094, Ukraine
  • Михаил В. Вовк Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., Kyiv 02660, Ukraine

DOI:

https://doi.org/10.1007/5570

Keywords:

5-aminopyrazolo[4, 3-b]pyridines, cyanoacetamide, 5-formylpyrazol-4-amines, imidazo[1, 2-a]pyrazolo[3, 4-e]pyridines, malononitrile, pyrazolo[3', 4', 5, 6]pyrido[2, 3-d]pyrimidines, cyclocondensation.

Abstract

1-Alkyl-N-Boc-5-formylpyrazol-4-amines react with malononitrile and cyanoacetamide to form 5-amino-1H-pyrazolo[4,3-b]pyridine nitriles and amides, respectively. Cyclocondensation of the obtained derivatives with chloroacetaldehyde, bromotrifluoroacetone, or ethyl bromopyruvate leads to the formation of imidazo[1,2-a]pyrazolo[3,4-e]pyridines or to pyrazolo[3',4',5,6]pyrido[2,3-d]pyrimidine derivatives in cyclocondensation with orthoesters, ethyl oxalyl chloride, or carbonyldiimidazole.

Author Biography

Михаил В. Вовк, Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., Kyiv 02660, Ukraine

Professor

Published

2020-04-01

Issue

Section

Original Papers