A CONVENIENT SYNTHESIS OF METHYL 4-OXO-4,5-DIHYDROPYRAZOLO[1,5-<i>a</i>]PYRAZINE-7-CARBOXYLATES AND CORRESPONDING CARBOXYLIC ACIDS

Authors

  • Nazar M. Tsyzoryk Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Akademika Kukharya St., Kyiv 02094, Ukraine
  • Andriy V. Bol'but Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Akademika Kukharya St., Kyiv 02094, Ukraine
  • Khrystyna I. Loza Enamine Ltd., 78 Winston Churchill St., Kyiv 02094, Ukraine
  • Vadym O. Dydko Enamine Ltd., 78 Winston Churchill St., Kyiv 02094, Ukraine
  • Ruslan V. Symchak Ternopil Volodymyr Hnatiuk National Pedagogical University, 2 Maksima Krivonosa St., Ternopil 46027, Ukraine
  • Yurii V. Dmitriv Enamine Ltd., 78 Winston Churchill St., Kyiv 02094, Ukraine National Technical University of Ukraine ''Igor Sikorsky Kyiv Polytechnic Institute'', 37 Peremohy Ave, Kyiv 03056, Ukraine
  • Mykhailo V. Vovk Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Akademika Kukharya St., Kyiv 02094, Ukraine

DOI:

https://doi.org/10.1007/7833

Keywords:

7-iodopyrazolo[1, 5-a]pyrazine-4(5H)-ones, palladium-catalyzed carbonylation, methyl-4-oxo-4, 5-dihydropyrazolo[1, 5-a]pyrazine-7-carboxylates, 4-oxo-4, 5-a]pyrazine-7-carboxylic acids.

Abstract

Pyrazolo[1,5-a]pyrazin-4(5H)-ones react regioselectively with N-iodosuccinimide in the presence of N-methylmorpholine to form 7-iodo derivatives. Their carbonylation catalyzed with Pd(dppf)Cl2 under pressure in MeOH solution yielded methyl 4-oxo-4,5-dihydropyrazolo[1,5-a]pyrazine-7-carboxylates, which were transformed into the corresponding carboxylic acids by alkaline hydrolysis.

Author Biography

Nazar M. Tsyzoryk, Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Akademika Kukharya St., Kyiv 02094, Ukraine

research scientist

 

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Published

2023-08-09

Issue

Vol. 59 No. 6/7 (2023): Ukrainian impact on heterocyclic chemistry after the three decades of independence

Section

Original Papers