A facile solid-phase synthesis of 1,2,4,5-tetrasubstituted imidazoles using sodium benzenesulfinate as a traceless linker.
The preparation of substituted imidazoles, thiazoles, and oxazoles using traceless solid-phase sulfone linker strategy is described. Key steps involved are (i) sulfinate acidification, (ii) sulfinic acid condensation with aldehyde and amine, and (iii) traceless product release by a one-pot elimination-cyclization reaction. The elimination reaction was carried out in the presence of a thiazolium catalyst that facilitated the in situ formation of the alpha-ketoamide, which was subsequently converted to the corresponding imidazoles, oxazoles, and thiazoles by treatment with amines, PPh(3)/I(2) or Lawesson's reagent. A library of 18 compounds was synthesized.
Li
Weiwei
W
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543.
Lam
Yulin
Y
D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D010080:Oxazoles / Q000138:chemical synthesis / Q000737:chemistry; D012964:Sodium / Q000737:chemistry; D013441:Sulfinic Acids / Q000737:chemistry*; D013844:Thiazoles / Q000138:chemical synthesis / Q000737:chemistry
D007093:Imidazoles; D010080:Oxazoles; D013441:Sulfinic Acids; D013844:Thiazoles; C425152:benzenesulfinic acid; D012964:Sodium