72149-83-8Relevant academic research and scientific papers
A convenient one-pot synthesis of thiazol-2-imines: application in the construction of pifithrin analogues
Murru, Siva,Singh,Kavala, Veerababurao,Patel, Bhisma K.
, p. 1931 - 1942 (2008/09/17)
For the first time a reaction intermediate has been isolated giving further insight into the mechanism of thiazol-2-imine formation. The first step of the reaction requires a basic medium, while the second step is an acid mediated E1 elimination reaction. An efficient one-pot synthesis of substituted thiazol-2-imines have been achieved by the condensation of carbonyl compounds with thioureas and 1,3-disubstituted thioureas using 1,1′-(ethane-1,2-diyl)dipyridinium bistribromide (EDPBT). Unsymmetrical 1,3-disubstituted thioureas give regioselective products with symmetrical ketones, which are mainly governed by the pKas of NH protons of thiourea, whereas symmetrical 1,3-disubstituted thioureas give regioselective products with symmetrical carbonyl compounds owing to the regioselective bromination of ketones. The methodology is extended to access novel neurodegenerative drug candidate pifithrin-α analogues in good yields in shorter reaction time. This method is simple, versatile and is applicable for different 1,3-disubstituted thioureas as well as a range of carbonyl compounds.
Synthesis and crystal structure of some novel 2-aroylimino-3-aryl-4-phenyl- 1,3-thiazolines
Saeed, Aamer,Zaman, Sabah,Bolte, Michael
, p. 2185 - 2199 (2008/09/21)
An efficient synthesis of some novel 2-aroylimino-3-aryl-4-phenyl-1,3- thiazolines was carried out by base-catalyzed cyclization of 1-aroyl-3-arylthioureas with acetophenone in the presence of bromine. The structures were confirmed by spectroscopic data,
3-Aryl-1-benzoylthioureas with α-bromoketones in water form 2-N-benzoyl-3-arylthiazol-2(3H)-imines, not 3-aryl-l-benzoylimidazoline-2- thiones
Singh,Murru, Siva,Kavala, Veerababurao,Patel, Bhisma K.
, p. 136 - 137 (2008/02/07)
The products obtained by the reaction of 1-benzoyl-3-phenylthioureaswith a-bromoketones in water in the presence of triethylamine are not imidazoline-2-thiones as reported (J. Chem. Res. 2005, 689-690); rather they are thiazol-2-imine derivatives.
One-pot synthesis of 2-acylimino-3-aryl-thiazoline derivatives in aqueous media
Wang, Xicun,Wang, Fang,Quan, Zhengjun,Zhang, Zhang,Wang, Mangang
, p. 2453 - 2460 (2007/10/03)
A one-pot, two-step synthesis for acyliminothiazolines by treated N,N′-substituted thioureas with α-bromocarbonyl compounds under aqueous media was described. Compared to the classical reaction in organic solvents, this method consistently has the advanta
It is "thiazolidene-2-imine" and not imidazole-2-thione as the reaction product of 1-benzoyl-3-phenylthiourea with Br2/enolizable ketone
Singh,Murru, Siva,Kavala, Veerababurao,Patel, Bhisma K.
, p. 5397 - 5399 (2007/10/03)
The products obtained by the reaction of benzoyl-3-phenylthioureas with bromine and enolizable ketones in the presence of triethylamine are not imidazole-2-thione derivatives as reported (Org. Lett. 2003, 5, 1657-1659) rather they are thiazolidene-2-imine
Microwave-accelerated, three-component, one-step synthesis of 2-acylimino-3-aryl-3H-thiazolines under solvent-free conditions
Xia, Min,Lu, Yue-Dong
, p. 1637 - 1643 (2007/10/03)
2-Acylimino-3-aryl-3H-thiazoline derivatives could be generated in excellent yields through three-component condensations of aroylisothiocyanates, primary amines, and ω-haloacetophenone under solvent-free microwave irradiation. Copyright Taylor & Francis Group, LLC.
