247224-14-2

Upstream product

• 55796-74-2 (benzylsulfanyl)methanimidamide hydrobromide 
• 100-39-0 benzyl bromide 
• 247224-05-1 2-(2-benzylmercapto-4-phenyl-imidazol-1-yl)-1-phenyl-ethanone 
• 247224-11-9 2-(2-benzylsulfanyl-4-phenyl-imidazol-1-yl)-1-phenyl-ethanol 

Relevant academic research and scientific papers

Synthesis of novel 2,3-dihydroimidazo[2,1-b][1,3]oxazoles through intramolecular nucleophilic ipso-substitution in 2-alkylsulfonylimidazoles

Readily available 2-(benzylsulfanyl)imidazoles 6, were studied as potential precursors toward the synthesis of novel diversely substituted 2,3-dihydroimidazo[2,1-b][1,3]oxazoles. Thus, the reaction between enolates derived from 6 and different electrophiles as well as the addition of Grignard reagents to the carbonyl group in 6 were explored. The formation of the fused imidazoxazoles 20 under mild conditions was successfully accomplished taking advantage of the key role played by the 2-alkylsulfonyl moiety in 19 as an efficient leaving group in intramolecular nucleophilic ipso-substitution reactions.

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

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.