Open Access Open Access  Restricted Access Subscription Access

A SIMPLE SYNTHESIS OF TRIFLUOROMETHYLATED PYRIDINIUM AZOMETHINE YLIDES BY THREE-COMPONENT REACTION BETWEEN PYRIDINES, PHENACYL BROMIDES, AND N-ARYLTRIFLUOROACETIMIDOYL CHLORIDES

Mahdiyeh Talebizadeh, Mohammad Anary-Abbasinejad, Ali Darekordi
Cover Image

Abstract


A novel synthesis of trifluoromethylated pyridinium azomethine ylides by three-component reaction between pyridines, phenacyl bromides, and trifluoromethylated imidoyl chlorides in acetonitrile as solvent at room temperature without any catalyst is described. The FT-IR, 1H, 13C, 19F NMR spectral and elemental analysis confirm the structures of products. The synthesized azomethine ylides are easily purified by washing with diethyl ether and are stable even at high temperature. Heating of these ylides in refluxing acetonitrile, ethanol, or DMSO did not result in the intramolecular cyclization to imidazopyridine derivatives and only starting ylides were isolated.


Keywords


imidoyl chlorides; pyridinium azomethine ylides; trifluoromethylated pyridinium azomethine ylides; phenacyl bromides; three-component reaction

Full Text: PDF Supplementary File(s): supplementary info (1MB)


 

 

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