569350-52-3

Upstream product

• 536-38-9 4-chlorobenzoylmethyl bromide 
• 121876-98-0 1,3-Bis-[1-dimethylamino-meth-(E)-ylidene]-thiourea 

Downstream Products

• 1384188-40-2 3-(p-chlorobenzoyl)-5-(1,2-O-isopropylidene-3-O-tert-butyldimethylsilyl-α-D-xylofuranos-5-ulo-5-yl)imidazo[2,1-b]thiazole 
• 1384188-42-4 3-(p-chlorobenzoyl)-5-(1,2-O-isopropylidene-3-O-p-methoxybenzyl-α-D-xylofuranos-5-ulo-5-yl)imidazo[2,1-b]thiazole 

Relevant academic research and scientific papers

From thiourea to bicyclic structures: An original route to imidazo[2,1-b]thiazoles, 5H-thiazolo[3,2-a]pyrimidines, 7H-imidazo[2,1-b][1,3]thiazines, and 2H,6H-pyrimido[2,1-b][1,3]thiazines

We report an example of an efficient regioselective synthesis of biheterocyclic compounds using thiourea as starting material. In fact, N,N′-bis(dimethylaminomethylene)thiourea (1), easily prepared by double condensation of N,N-dimethylformamide dimethyl acetal with thiourea, can be reacted with haloketones or acrylic dienophiles to give thiazolic (2) and thiazinic (3) diazadienes, respectively, themselves undergoing cyclization reactions to yield imidazo[2,1-b]thiazoles, 5H-thiazolo[3,2-a]pyrimidines, 7H-imidazo[2,1-b][1,3]thiazines, and 2H,6H-pyrimido[2,1-b][1,3]thiazines without any regioisomeric ambiguity. This straightforward route represents an original and unambiguously regioselective pathway to these valuable heterocycles.