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A THREE-COMPONENT SYNTHESIS OF TRIFLUOROMETHYLATED HEXAHYDROPYRROLO[1,2-a]IMIDAZOL-5-ONES AND HEXAHYDROPYRROLO[1,2-a]PYRIMIDIN-6-ONES

Марина В. Горяева, Олеся А. Фефелова, Янина В. Бургарт, Марина А. Ежикова, Михаил И. Кодесс, Павел А. Слепухин, Галина А. Триандафилова, Сергей Ю. Солодников, Ольга П. Красных, Виктор И. Салоутин
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Abstract


A three-component reaction of ethyl trifluoropyruvate, methyl ketones, and ethylenediamine or 1,3-diaminopropane afforded hexahydropyrrolo[1,2-a]imidazol-5-ones and hexahydropyrrolo[1,2-a]pyrimidin-6-ones. When using an excess of ethyl trifluoropyruvate in reactions with acetone and diamines, dipyrrolo[1,2-a:2',1'-b]imidazole-3,8-dione and dipyrrolo[1,2-a:2',1'-b]pyrimidine-3,9-dione were obtained. An aldol mechanism for the formation of the bi- and tricyclic compounds was proposed, and their diastereomeric structure was established. Some of the obtained heterocycles were found to possess analgesic activity.

Authors: Marina V. Goryaeva, Olesya А. Fefelova, Yanina V. Burgart, Marina А. Ezhikova, Mikhail I. Kodess, Pavel А. Slepukhin, Galina А. Triandafilova,
Sergey Yu. Solodnikov, Olga P. Krasnykh, Victor I. Saloutin*


Keywords


diamines; dipyrrolo[1,2-a:2',1'-b]imidazole-3,8-dione; dipyrrolo[1,2-a:2',1'-b]pyrimidine-3,9-dione; ethyl trifluoropyruvate; hexahydropyrrolo[ 1,2-a]imidazol-5-ones; hexahydropyrrolo[1,2-a]pyrimidin-6-ones; methyl ketones; analgesic activity; three-component reaction

Full Text: PDF (Russian) Supplementary File(s): Supporting information (2MB)


 

 

Latvian Institute of Organic Synthesis - Aizkraukles iela, 21, Riga, LV-1006, Latvia - hgs@osi.lv