ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Synthesis of 4-(Benzylthio)-and 4-(Arylthio)-1,3-oxazole-5(2H)-onesFollowing a known procedure, 4-(benzylthio)-1,3-oxazol-5(2H)-one (4a) was synthesized starting from sodium cyanodithioformate (1) and cyclohexanone (Scheme 1). The structure of the intermediate 4-(benzylthio)-1,3-thiazol-5(2H)-one (3a) was established by X-ray crystallography. An alternative route was developed for the synthesis of 4-(arylthio)-1,3-oxazol-5(2H)-ones which are not accessible by the former reaction. Treatment of ethyl cyanoformate (5) with a thiophenol in the presence of catalytic amounts of Et2NH and TiCl4, followed by addition of a ketone and BF3.Et2O in a one-pot-reaction, gave 4f-i in low-to-fair yields (Scheme 3). Both synthetic pathways-complementary as for benzyl-S and aryl-S derivatives-seem to be limited with respect to variation of substituents of the ketone.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19870700518
