55114-48-2

Upstream product

• 96-45-7 N,N'-ethylenethiourea 
• 78-95-5 chloroacetone 
• 96-45-7 4,5-dihydro-1H-imidazole-2-thiol 
• 75697-82-4 7-(4-chlorobenzenesulphonyl)-3-methyl-5,6-dihydroimidazolo<2,1-b>thiazolium chloride 

Downstream Products

• 139313-12-5 3-methyl-7-<2-(4'-bromophenyl)-2-oxoethyl>-5,6-dihydroimidazo<2,1-b>thiazolium bromide 
• 139313-11-4 3-methyl-7-(2-phenyl-2-oxoethyl)-5,6-dihydroimidazo<2,1-b>thiazolium bromide 
• 139313-13-6 3-methyl-7-(2-ethoxy-2-oxoethyl)-5,6-dihydroimidazo<2,1-b>thiazolium bromide 
• 75697-87-9 7-(4-Chloro-benzoyl)-3-methyl-5,6-dihydro-imidazo[2,1-b]thiazol-7-ium; chloride 

Relevant academic research and scientific papers

THIAZOLINE DERIVATIVE AND USE OF THE SAME

A thiazoline derivative represented by Formula (I): wherein R is a cyclic hydrocarbon group which may be substituted, or a heterocyclic group which may be substituted; X is a bond or a divalent chain hydrocarbon group which may be substituted; X' is a bond or -N(R5)-; Y is a divalent hydrocarbon group which may be substituted; Y' is a bond or -C(=O)-; ring A is a nitrogen-containing heterocycle which may be substituted; Z1 and Z3 are each independently a bond or a divalent chain hydrocarbon group which may be substituted; Z2 is a bond or -N(R6)-; and B is a group represented by the formula: which is useful as a therapeutic drug for thrombosis, is provided.

Steroidal Heterocycles: Synthesis and Structure of Imidazothiazolo-, Thiazolobenzimidazolo-, and Thiazolo-s-triazolo-derivatives

The condensation of 2α-bromo-5α-cholestan-3-one (1) with 2-mercaptoimidazole (2) in refluxing ethanol gave 5α-cholest-2-eno-(imidazothiazole) (5) and 3β-ethoxy-2'β,3'-dihydro-5α-cholestano-(imidazothiazole) (6), whereas the reaction of 2-mercaptoimidazole (2) with 16α-bromo-3-methoxyestra-1,3,5(10)-trien-17-one (7) gave the uncyclised product 16α-(imidazol-2-ylthio)-3-methoxyestra-1,3,5(10)-trien-17-one (8).Under analogous reaction conditions, the condensation of 2-mercaptoimidazole (2), 2-mercaptobenzimidazole (12), 3-mercapto-1,2,4-triazole (35), and their derivatives with 2α-bromo-3-oxo-steroids gave the expected cyclised products.However, from the condensation reactions between 3-mercapto-1,2,4-triazoles (35) and (36) with the 16α-bromo-17-oxo steroid (7) only 17β-ethoxy-3-methoxy-5',6'-dihydro-(thiazolo--s-triazole) (44) and its 2'-methyl derivative (45) were isolated.The structures of all the condensation products were determined with the help of i.r., 1H n.m.r., and 13C n.m.r. spectroscopy.

7-Alkylation and 7-Sulphonylation of 5,6-Dihydroimidazolo-thiazoles

Reinvestigation of the alkylation of 3-phenyl-5,6-dihydroimidazolothiazole has shown that methylation occurs exclusively at the 7-position, and that the free base is readily solvolysed to a mixture of 1-methylimidazolidin-2-one, 1-methylimidazolidine-2-thione, and diphenacyl sulphide and disulphide. 3-Methyl-5,6-dihydroimidazolothiazole with methane- and arene-sulphonyl chlorides gave the corresponding 7-sulphonylthiazolium chlorides.On heating, these rearranged to 3-(2-chloroethyl)-4-methyl-3-aryl (or alkyl)sulphonylimido-2,3-dihydrothiazoles.The 7-(4-chlorophenylsulphonyl) derivative lost this substituent with aqueous base while concentrated aqueous ammonia attacked the 7a-position leading to a 3--2-imino-4-methyl-2,3-dihydrothiazole.