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Regioselectivity of SNAr reactions in the synthesis of isomeric difluorinated 4- and 6-piperidino-5-azaindoles

Larisa Yur'evna Gurskaya 1
Larisa Yur'evna Gurskaya
, 
Irina Vladimirovna Beregovaya 1
Irina Vladimirovna Beregovaya
, 
Igor Petrovich Chuikov 1
Igor Petrovich Chuikov
, 
Boris Alekseevich Selivanov 1
Boris Alekseevich Selivanov
, 
Larisa Vladimirovna Politanskaya 1
Larisa Vladimirovna Politanskaya
10.71267/mencom.7780
Published 2025-10-21
Communication , Volume 35, Issue 6, 645-647
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Gurskaya L. Y. et al. Regioselectivity of SNAr reactions in the synthesis of isomeric difluorinated 4- and 6-piperidino-5-azaindoles // Mendeleev Communications. 2025. Vol. 35. No. 6. pp. 645-647.
GOST all authors (up to 50) Copy
Gurskaya L. Y., Beregovaya I. V., Chuikov I. P., Selivanov B. A., Politanskaya L. V. Regioselectivity of SNAr reactions in the synthesis of isomeric difluorinated 4- and 6-piperidino-5-azaindoles // Mendeleev Communications. 2025. Vol. 35. No. 6. pp. 645-647.
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TY - JOUR
DO - 10.71267/mencom.7780
UR - https://mendcomm.colab.ws/publications/10.71267/mencom.7780
TI - Regioselectivity of SNAr reactions in the synthesis of isomeric difluorinated 4- and 6-piperidino-5-azaindoles
T2 - Mendeleev Communications
AU - Gurskaya, Larisa Yur'evna
AU - Beregovaya, Irina Vladimirovna
AU - Chuikov, Igor Petrovich
AU - Selivanov, Boris Alekseevich
AU - Politanskaya, Larisa Vladimirovna
PY - 2025
DA - 2025/10/21
PB - Mendeleev Communications
SP - 645-647
IS - 6
VL - 35
ER -
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@article{2025_Gurskaya,
author = {Larisa Yur'evna Gurskaya and Irina Vladimirovna Beregovaya and Igor Petrovich Chuikov and Boris Alekseevich Selivanov and Larisa Vladimirovna Politanskaya},
title = {Regioselectivity of SNAr reactions in the synthesis of isomeric difluorinated 4- and 6-piperidino-5-azaindoles},
journal = {Mendeleev Communications},
year = {2025},
volume = {35},
publisher = {Mendeleev Communications},
month = {Oct},
url = {https://mendcomm.colab.ws/publications/10.71267/mencom.7780},
number = {6},
pages = {645--647},
doi = {10.71267/mencom.7780}
}
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Gurskaya, Larisa Yur'evna, et al. “Regioselectivity of SNAr reactions in the synthesis of isomeric difluorinated 4- and 6-piperidino-5-azaindoles.” Mendeleev Communications, vol. 35, no. 6, Oct. 2025, pp. 645-647. https://mendcomm.colab.ws/publications/10.71267/mencom.7780.
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Keywords

5-azaindoles
aminodefluorination
electrophilic iodination
heterocyclization
organofluorine compounds
quantum chemical calculations.
regioselectivity
SNAr reactions
Sonogashira cross-coupling

Abstract

For the targeted synthesis of fluorinated analogues of 5-azaindoles used for the prevention and treatment of diabetes and obesity, the regioselectivity of fluorine replacement by piperidine residue in their precursors is explored. The reverse sequence of the SNAr reaction and cyclization steps enables the selective preparation of isomeric 5-azaindoles containing substituents at positions 4 vs. 6, respectively. A quantum-chemical justification of the predominant positions of nucleophilic attack in polyfluoroarenes is given.

Funders

Ministry of Education and Science of the Russian Federation
075-00365-25-00