Improved Syntheses of Vinyl Imidazoles1

Abstract A series of vinylimidazoles were synthesized via Wittig reactions on N-tritylimidazole-4-carboxaldehyde. Activated phosphonate ylids afforded yields in excess of 90% while the yields from unactivated ylids ranged from 10–82%. The trityl group may be removed by mild acid hydrolysis in high yield.

[1]  J. Kokosa,et al.  Practical multigram synthesis for 4(5)-vinylimidazole , 1983 .

[2]  G. Kavadias,et al.  Synthesis of 4,5-disubstituted imidazoles , 1982 .

[3]  S. Morita,et al.  Conformational and neighboring effects in graft polymerization of acrolein onto imidazole-containing polymer , 1982 .

[4]  B. Torian,et al.  PREPARATION AND STEREOCHEMISTRY OF 4-ARYL-3-BUTENYLAMINES. A NOVEL SYNTHESIS OF AN OXAZOLO(2,3-A)ISOINDOLE , 1981 .

[5]  K. Honda,et al.  Convenient synthesis of alkyl esters of urocanic acid. , 1981, Journal of pharmaceutical sciences.

[6]  S. Morita,et al.  Polymer effect in graft polymerizations of acrolein onto imidazole‐containing polymer , 1980 .

[7]  F. Texier-Boullet,et al.  The Wittig-Horner Reaction in Solid-Liquid Two Phase Systems , 1979 .

[8]  C. Overberger,et al.  Esterolytic activity of imidazole‐containing polymers. Synthesis and characterization of copoly[1‐alkyl‐4‐ or 5‐vinylimidazole/4(5)‐vinylimidazole] and its catalytic activity in the hydrolysis of p‐nitrophenyl acetate , 1978 .

[9]  J. Beisler,et al.  Synthesis and antitumor properties of some isoindolylalkylphosphonium salts. , 1978, Journal of medicinal chemistry.

[10]  J. Kelley,et al.  Attempted inhibition of histidine decarboxylase with beta-alkyl analogues of histidine. , 1977, Journal of medicinal chemistry.

[11]  W. Schunack.  Ester des 4‐Hydroxymethyl‐imidazols und der 4‐Imidazolessigsäure 2. Mitt. über Struktur‐Wirkungs‐Beziehungen bei Histaminanaloga , 1974 .

[12]  A. Burger,et al.  2-(4-imidazolyl)cyclopropylamine. , 1970, Journal of medicinal chemistry.