247224-22-2Relevant academic research and scientific papers
A new class of fused imidazoles by intramolecular nucleophilic ipso- substitution in 2-alkylsulfonylimidazoles: Synthesis of 2,3- dihydroimidazo[2,1-b][1,3]oxazoles
Heras, Montserrat,Ventura, Montserrat,Linden, Anthony,Villalgordo, José M.
, p. 1613 - 1624 (1999)
Starting from readily available thiouronium salts 1 and α-halocarbonyl compounds 2, a simple and efficient synthesis of 2-alkylthioimidazoles 3 was accomplished. Reduction of the carbonyl group, followed by oxidation of the 2-alkylthioether moiety, afforded sulfones 8. Intramolecular nucleophilic ipso-substitution in 2-alkylsulfonylimidazoles 8 efficiently furnished a novel class of fused imidazoxazoles. This finding was extended towards the generation in solution of a small library of 2,3-dihydroimidazo[2,1- b][1,3]oxazoles.
