The Synthesis Of Thiazolidine-2-one Through Reaction Of 1,4-dithiane-2,5-diol And Acyl Azide

The heterocyclic systems exist in a large number of drugs and biologically related molecules.The substituted thiazole-one fragment is a structural motif in a huge number of drugs,natural and synthetic products.Most of these compounds show significant application value.Therefore,a great deal of attention has been given to its organic synthesis.Despite there are many reports on the synthesis of thiazole-one,the reported methods still have many problems such as difficult access to raw materials,low yileds,and poor applicability to the functional groups.The established methods for more facile and general construction of thiazole-one remain in demand.In this paper,we developed a method to provide 4-hydroxy-3-arylthiazolidine-2-one and 3-arylthiazol-2?3H?-one via acyl azide and 1,4-dithiane-2,5-diol.Additives,solvent,temperature,equivalent were selected as conditions in order to optimize the conditions of the reaction:benzoyl azide and 1,4-dithiane-2,5-diol?eq:1:0.55?were conducted in MeCN at 80?for 21 h.A series of 4-hydroxy-3-arylthiazolidine-2-one compounds were obtained in yields of 72%-90%.Furthemore the tentative mechanism is proposed,we have also developed a rapid access to 3-arylthiazol-2?3H?-one through dehydration.We attempted to construted a new method for the synthesis of hydantoin through acyl azide and glycine.The reaction provides 4-hydroxy-3-arylthiazolidine-2-one in good yields with the advantages of operational simplicity and a satisfactory substrate scope,easily available raw materials.A new method for the synthesis of 4-hydroxy-3-substituted-thiazolidine-2-one by one-pot reaction of 2,5-dihydroxy-1,4-dithiane and acyl azide has been developed.The compounds obtained in the experiment were characterized by ¹HNMR,¹³CNMR and HRMS,and their biological evaluation was also under way.