Synthesis of 6-azaindoles <i>via</i> formal electrophilic [4 + 1]-cyclization of 3-amino-4-methyl pyridines: new frontiers of diversity

Ivonin, Sergey P.; Voloshchuk, Volodymyr V.; Rusanov, Eduard B.; Suikov, Sergiy; Ryabukhin, Serhiy V.; Volochnyuk, Dmytro M.

doi:10.1039/d3qo01937c

Cited by 1 publication

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“…This method was demonstrated to be very effective, scalable, and regioselective, requiring no catalysts and quite easy to perform. Also, the same year, the synthesis of 6-azaindoles via the formal electrophilic [4+1]-cyclization of 3-amino-4-methyl pyridines from the whole set of 3-amino-4-methylpyridine derivatives was described in detail (Scheme 17) [34]. The essential difference compared to all similar reactions previously known is the absence of the activation of the methyl group by a strong base.…”

Section: Annulation Of the Pyrrole Nuleus To The Pyridine Cyclementioning

confidence: 99%

Recent Advances in the Synthesis and Biological Activity of Pyrrolo[2,3-c]pyridines

Voloshchuk,

Ivonin

2024

J. Org. Pharm. Chem.

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Pyrrolo[2,3-c]pyridines (6-azaindoles) are the most promising nitrogen-containing heterocyclic compounds in the field of drug development. Exhibiting extraordinary versatility as pharmacophores, they are widely used in the development of kinase inhibitors, antiproliferative agents, and as potential therapeutic agents for the treatment of various diseases, including cancer and Alzheimer’s disease. A large number of works focusing on new methods and approaches in the synthesis of 6-azaindoes, as well as on the study of their biological activity, have been published worldwide. In our review, we tried to classify all currently known strategies for the construction of the 6-azaindole core, which were published within the last 15 years, the chemical diversity of the derivatives obtained, and their therapeutic potential in the context of medicinal chemistry. We hope that this work will generalize and facilitate the understanding of the strategy for the synthesis of pyrrolo[2,3-c]pyridines, as well as help scientists in their further research in the direction of 6-azaindoles.

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Section: Annulation Of the Pyrrole Nuleus To The Pyridine Cyclementioning

confidence: 99%

Recent Advances in the Synthesis and Biological Activity of Pyrrolo[2,3-c]pyridines

Voloshchuk,

Ivonin

2024

J. Org. Pharm. Chem.

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Synthesis of 6-azaindoles via formal electrophilic [4 + 1]-cyclization of 3-amino-4-methyl pyridines: new frontiers of diversity

Abstract: A scalable and efficient synthesis of the 2-trifluoromethyl-3-trifluoroacetyl-6-azaindoles from 3-amino-4-methylpyridines under treatment with TFAA was disclosed. The reaction scope and limitation towards the pyridine and electrophilic components were investigated. Activation...

Cited by 1 publication

References 18 publications

Recent Advances in the Synthesis and Biological Activity of Pyrrolo[2,3-c]pyridines

Recent Advances in the Synthesis and Biological Activity of Pyrrolo[2,3-c]pyridines

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