Switching Imidazolinones from Electrophiles to Nucleophiles: Synthesis of 4-(Pyrrolidin-2-yl)imidazole-2-ones via Regioselective Electrophilic Addition / Deprotonation Reaction
نویسندگان
1 FRC Kazan Scientific Center, Russian Academy of Science, Arbuzov Institute of Organic and Physical Chemistry, Kazan 420088, Russia
2 Organic Chemistry Department, Butlerov Chemistry Institute, Kazan Federal University, Kazan 420008, Russia
3 FRC Kazan Scientific Center, Russian Academy of Science, Arbuzov Institute of Organic and Physical Chemistry, Kazan 420088, Russia
4 Laboratory of Engineering Profile, Korkyt Ata Kyzylorda University, Kyzylorda 120014, Kazakhstan
5 Laboratory of Engineering Profile, Korkyt Ata Kyzylorda University, Kyzylorda 120014, Kazakhstan
6 CNEC LLP, Kyzylorda 120001, Kazakhstan
7 FRC Kazan Scientific Center, Russian Academy of Science, Arbuzov Institute of Organic and Physical Chemistry, Kazan 420088, Russia
8 FRC Kazan Scientific Center, Russian Academy of Science, Arbuzov Institute of Organic and Physical Chemistry, Kazan 420088, Russia
9 FRC Kazan Scientific Center, Russian Academy of Science, Arbuzov Institute of Organic and Physical Chemistry, Kazan 420088, Russia
10 FRC Kazan Scientific Center, Russian Academy of Science, Arbuzov Institute of Organic and Physical Chemistry, Kazan 420088, Russia
11 Laboratory of Engineering Profile, Korkyt Ata Kyzylorda University, Kyzylorda 120014, Kazakhstan
12 CNEC LLP, Kyzylorda 120001, Kazakhstan
doi
10.48309/chemm.2026.539448.1998چکیده
Imidazolinones are known to react with nucleophiles in acidic media through intermediate iminium ion formation. In contrast, their interactions with electrophiles in acid-catalyzed systems are uncommon and have been scarcely documented. In this work, it was demonstrated that imidazolin-2-ones can function as nucleophiles in acid-promoted reactions with N-(4,4-diethoxybutyl)sulfonylamides, facilitating the regioselective preparation of 4-(pyrrolidin-2-yl)imidazole-2-ones. The target products were obtained in moderate to good yields (45–71%), with reactivity influenced by substituent effects.
