Ring Transformations of Heterocyclic Compounds. XVII [1]. 2-(2,4,6-Triarylphenyl) Substituted Dihydro-1H-imidazolium, Dihydrothiazolium and Thiazolium Salts from 2-Methyl Derivatives by Pyrylium and Thiopyrylium Ring Transformations

摘要

The synthesis of hitherto unknown 2-(2,4,6-triarylphenyl) substituted 4,5-dihydro-1H-imidazolium perchlorates 6, 4,5-dihydrothiazolium perchlorates 8 and thiazolium perchlorates 9 from their 2-methyl derivatives 2, 4 and 5, respectively, by a 2,6-[C_5+C] ring transformation of 2,4,6-triarylpyrylium and -thiopyrylium salts 1/10 in ethanol in the presence of an appropriate base (6: sodium ethanolate; 8,9: anhydrous sodium acetate) is reported. Spectroscopic data of the transformation products and structural influences on their formation via anhydrobases of the salts 2, 4 and 5 are discussed.