82202-31-1Relevant academic research and scientific papers
Small molecule library synthesis using segmented flow
Thompson, Christina M.,Poole, Jennifer L.,Cross, Jeffrey L.,Akritopoulou-Zanze, Irini,Djuric, Stevan W.
experimental part, p. 9161 - 9177 (2012/01/03)
Flow chemistry has gained considerable recognition as a simple, efficient, and safe technology for the synthesis of many types of organic and inorganic molecules ranging in scope from large complex natural products to silicon nanoparticles. In this paper
The Hantzsch Thiazole Synthesis under Acidic Conditions: Change of Regioselectivity
Bramley, (Miss) Susan E.,Dupplin, Viscount,Goberdhan, Dhanesh G. C.,Meakins, G. Denis
, p. 639 - 644 (2007/10/02)
The condensation of α-halogeno ketones with N-monosubstituted thioureas in neutral solvent leads exclusively to 2-(N-substituted amino)thiazoles.In the present work it was shown that under acidic conditions mixtures of 2-(N-substituted amino)thiazoles and 3-substituted 2-imino-2,3-dihydrothiazoles are formed. (The isomers were distinguished by characteristic differences between their 5-H 1H n.m.r. signals and the i.r.CO bands of their trifluoroacetate derivatives.) The proportions of the 2-imino-2,3-dihydrothiazoles in the mixtures are influenced by experimental features and by the structures of the starting materials.Reactions in 10 M-HCl-EtOH (1:2) at 80 deg C for 20 min were found to be the most efficient for generating 2-imino-2,3-dihydrothiazoles; in the most favourable case 2-imino-3,4-dimethyl-2,3-dihydrothiazole was obtained in 73 percent yield.A possible explanation of the results is discussed.
