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Late-stage N-functionalization of diazo NH-heterocycles: the Mitsunobu reaction vs. alkylation with alkyl halides

Natalia Igorevna Guranova 1
Natalia Igorevna Guranova
, 
Grigoriy Pavlovich Kantin 1
Grigoriy Pavlovich Kantin
, 
Olga Yurievna Bakulina 1
Olga Yurievna Bakulina
, 
Alexander Denisovich Yanovich 1
Alexander Denisovich Yanovich
, 
Dmitry Viktorovich Dar’in 1, 2
Dmitry Viktorovich Dar’in
1 Institute of Chemistry, St. Petersburg State University, 198504 St. Petersburg, Russian Federation
2 St. Petersburg Research Institute of Phthisiopulmonology, 191036 St. Petersburg, Russian Federation
10.71267/mencom.7586
Published 2025-02-18
Communication , Volume 35, Issue 2, 165-168
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Guranova N. I. et al. Late-stage N-functionalization of diazo NH-heterocycles: the Mitsunobu reaction vs. alkylation with alkyl halides // Mendeleev Communications. 2025. Vol. 35. No. 2. pp. 165-168.
GOST all authors (up to 50) Copy
Guranova N. I., Kantin G. P., Bakulina O. Y., Yanovich A. D., Dar’in D. V. Late-stage N-functionalization of diazo NH-heterocycles: the Mitsunobu reaction vs. alkylation with alkyl halides // Mendeleev Communications. 2025. Vol. 35. No. 2. pp. 165-168.
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TY - JOUR
DO - 10.71267/mencom.7586
UR - https://mendcomm.colab.ws/publications/10.71267/mencom.7586
TI - Late-stage N-functionalization of diazo NH-heterocycles: the Mitsunobu reaction vs. alkylation with alkyl halides
T2 - Mendeleev Communications
AU - Guranova, Natalia Igorevna
AU - Kantin, Grigoriy Pavlovich
AU - Bakulina, Olga Yurievna
AU - Yanovich, Alexander Denisovich
AU - Dar’in, Dmitry Viktorovich
PY - 2025
DA - 2025/02/18
PB - Mendeleev Communications
SP - 165-168
IS - 2
VL - 35
ER -
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@article{2025_Guranova,
author = {Natalia Igorevna Guranova and Grigoriy Pavlovich Kantin and Olga Yurievna Bakulina and Alexander Denisovich Yanovich and Dmitry Viktorovich Dar’in},
title = {Late-stage N-functionalization of diazo NH-heterocycles: the Mitsunobu reaction vs. alkylation with alkyl halides},
journal = {Mendeleev Communications},
year = {2025},
volume = {35},
publisher = {Mendeleev Communications},
month = {Feb},
url = {https://mendcomm.colab.ws/publications/10.71267/mencom.7586},
number = {2},
pages = {165--168},
doi = {10.71267/mencom.7586}
}
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Guranova, Natalia Igorevna, et al. “Late-stage N-functionalization of diazo NH-heterocycles: the Mitsunobu reaction vs. alkylation with alkyl halides.” Mendeleev Communications, vol. 35, no. 2, Feb. 2025, pp. 165-168. https://mendcomm.colab.ws/publications/10.71267/mencom.7586.

Keywords

N-alkylation
alkyl halides
diazo carbonyl compounds
Mitsunobu reaction
NH-heterocycles

Abstract

Selective N-alkylation of various diazo NH-heterocycles with preserving the diazo function was performed either by classical alkylation with alkyl halides or by the Mitsunobu reaction with alcohols. The substrate variety involved diazo-substituted homophthalimide, arylidenesuccinimides, (thio)barbituric acids, and pyrazolones. This is the first time the Mitsunobu reaction has been applied for the functionalization of diazo carbonyl compounds.

Funders

Russian Science Foundation
20-13-00024

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