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Mendeleev Commun., 2025 Volume 35, Issue 2, Pages 165–168 (Mi mendc1369)

Communications

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

N. I. Guranovaa, G. P. Kantina, O. Yu. Bakulinaa, A. D. Yanovicha, D. V. Dar’inab

a Institute of Chemistry, St. Petersburg State University, 198504 St. Petersburg, Russian Federation
b St. Petersburg Research Institute of Phthisiopulmonology, 191036 St. Petersburg, Russian Federation

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.

Keywords: diazo carbonyl compounds, N-alkylation, Mitsunobu reaction, alkyl halides, NH-heterocycles.

Received: 06.08.2024
Accepted: 10.09.2024

Language: English

DOI: 10.71267/mencom.7586



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© Steklov Math. Inst. of RAS, 2025