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

• DOI: 10.71267/mencom.7586
• Publication Date: 2025-02-18T10:29:26Z
• Authors: Natalia Igorevna ...; Grigoriy Pavlovic...; Olga Yurievna Bak...; Alexander Denisov...; Dmitry Viktorovic...
• Keywords: Mitsunobu reaction; Surface Modification

Selective <em>N</em>-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.