4332-97-2Relevant articles and documents
Base controlled three-component regioselective synthesis of 2-imino thiazolines and 2-thioxoimidazolin-4-ones
Barve, Indrajeet J.,Chang, Wong-Jin,Lin, Yen-Tzu,Thikekar, Tushar Ulhas,Sun, Chung-Ming
, (2019/03/07)
Base-controlled regioselective synthesis of 2-imino thiazolines and 2-thioxoimidazolin-4-ones was achieved to use a one-pot reaction between chiral amino esters, isothiocyanates, and α-bromoketones/alkyl halides. This three-component coupling reaction in acetonitrile provides 2-imino thiazolines, whereas the formation of 2-thioxoimidazolin-4-ones was observed under basic conditions at ambient temperature. The corresponding products were obtained in good to excellent yield with broad substrate scope. Isolation of thiourea and thiohydantoin intermediates disclosed the course of the reaction mechanism.
Enantioselective Synthesis of 5,5-Disubstituted Hydantoins by Br?nsted Base/H-Bond Catalyst Assisted Michael Reactions of a Design Template
Izquierdo, Joseba,Etxabe, Julen,Du?abeitia, Eider,Landa, Aitor,Oiarbide, Mikel,Palomo, Claudio
supporting information, p. 7217 - 7227 (2018/05/04)
A new method for the enantioselective synthesis of 5,5-disubstituted (quaternary) hydantoins was developed on the basis of an organocatalytic Michael reaction approach involving the use of 2-benzylthio-3,5-dihydroimidazol-4-ones as key hydantoin surrogates. The method is general with respect to the substitution pattern at the hydantoin N1 (alkyl, aryl, acyl), N3 (aryl), and C5 (linear/branched alkyl, aryl) positions and affords essentially single diastereomeric products with enantioselectivities higher than 95 % ee in most cases. Among the bifunctional Br?nsted base/H-bond catalysts examined, a known squaramide–tertiary amine catalyst and a newly prepared squaramide–tertiary amine catalyst provide the highest selectivity so far with either nitroolefins or vinyl ketones as the acceptor components. Kinetic measurements support a first-order rate dependence on both reaction partners, the donor template and the Michael acceptor, whereas competitive 1H NMR spectroscopy experiments reveal the high ability of the template for catalyst binding.
An efficient method for synthesis of thiohydantoins with α-amino esters under microwave irradiation
Zhao, Yanmei,Wang, Zhouyu,Jiang, Zhenju,Feng, Hualin,Liu, Li,Wang, Ju
, p. 1171 - 1173 (2014/06/09)
An efficient and simple way for synthesis of thiohydantoins is reported. In the absence of any additional catalysts, a series of thiohydantoins were synthesized with amino esters and isothiocyanates in aqueous medium under microwave irradiation. Excellent isolated yields (up to 98 %) were obtained under mild conditions.