SYNTHESIS AND REACTIONS OF NOVEL IMIDAZO[4,5-<i>]</i>PYRIDINE BUILDING BLOCKS

Authors

  • Tetiana F. Dubina Enamine Ltd., Winston Churchill Street 78, Kyїv 02094
  • Anton V. Kosarevych Enamine Ltd., Winston Churchill Street 78, Kyїv 02094. Taras Shevchenko National University of Kyiv, Volodymyrska Street 60, Kyїv 01601
  • Olexandr V. Kucher Enamine Ltd., Winston Churchill Street 78, Kyїv 02094. V. P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry, National Academy of Sciences of Ukraine, Akademik Kukhar Street 1, Kyїv 02094
  • Bohdan S. Sosunovych Enamine Ltd., Winston Churchill Street 78, Kyїv 02094
  • Oleg B. Smolii V. P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry, National Academy of Sciences of Ukraine, Akademik Kukhar Street 1, Kyїv 02094
  • Bohdan V. Vashchenko Enamine Ltd., Winston Churchill Street 78, Kyїv 02094. Taras Shevchenko National University of Kyiv, Volodymyrska Street 60, Kyїv 01601
  • Oleksandr O. Grygorenko Enamine Ltd., Winston Churchill Street 78, Kyїv 02094. Taras Shevchenko National University of Kyiv, Volodymyrska Street 60, Kyїv 01601

Keywords:

imidazopyridines, purine bioisosteres, building blocks, coupling reactions, cyclization

Abstract

The synthesis of a novel imidazo[4,5-b]pyridine and its partially saturated derivative relied on Michael addition of 1-methyl-1H-imidazol-4-amine to fumaric/maleic or acetylene dicarboxylates, followed by intramolecular cyclization into target compounds. The common transformations of the resulting pyridine carboxylate were performed to obtain a series of building blocks, i.e. carboxylic acids, amides, and amines. The pyridone fragment was transformed into the fused bromopyridine moiety which was used for Buchwald–Hartwig and Suzuki cross-coupling reactions providing a versatile access to an extended scope of imidazopyridines. All synthesized building blocks could be considered as promising purine bioisosteres for the synthetic and medicinal chemistry.

Author Biography

Bohdan V. Vashchenko, Enamine Ltd., Winston Churchill Street 78, Kyїv 02094. Taras Shevchenko National University of Kyiv, Volodymyrska Street 60, Kyїv 01601

Currently:
- Assistant (Taras Shevchenko National University of Kyiv, 2022 to date)
- Senior Engineer (Taras Shevchenko National University of Kyiv, 2021 to date)
- PhD Student (Taras Shevchenko National University of Kyiv, 2019 to date)
- Researcher at Scientific Support Department (Enamine Ltd. 2018 to date)

Previous experience:
- Master's Degree (Taras Shevchenko National University of Kyiv, 2017—2019)
- Synthetic Chemist (Enamine Ltd., 2016—2018)
- Practicing Synthetic Chemist (Taras Shevchenko National University of Kyiv, 2014—2016)
- Bachelor's Degree (Taras Shevchenko National University of Kyiv, 2013—2017)

Scientific interests:
- organic synthesis, lead-oriented synthesis, building blocks for drug discovery, organosulfur (VI), -fluorine and -boron derivatives, alicyclic and heterocyclic compounds, combinatorial and medicinal chemistry, exit vector plots.

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Published

2024-05-28

Issue

Vol. 60 No. 3/4 (2024)

Section

Original Papers