Late-stage N-functionalization of diazo NH-heterocycles via alkylation by Mitsunobu reaction or with alkyl halides

• DOI: 10.3762/bxiv.2024.43.v1
• Publication Date: 2024-06-20T12:25:00Z
• Authors: Natalia Guranova; Grigory Kantin; Olga Bakulina; Alexander Yanovich; Dmitry Dar'in
• Keywords: Mitsunobu reaction; Surface Modification

a-Diazo carbonyl compounds are widely used as reagents of vast synthetic potential, capable delivering biologically relevant and diverse molecular scaffolds. Herein we present methods for selective N -alkylation various diazo NH-heterocycles while maintaining the function further modifications. homophthalimide, arylidene succinimides, barbituric thiobarbituric acids, a-diazo pyrazolones were readily alkylated with alkyl halides or alcohols under Mitsunobu reaction conditions. This is first time that has been applied functionalization compounds. The method expands scope substituents can be introduced into molecule, including such challenging moieties adamantyl, cholesteryl menthyl.