Hahn, HG Chang, KH Dal Nam, K Bae, SY Mah, H 2024-01-21T16:33:10Z 2024-01-21T16:33:10Z 2022-01-11 1998-11-01 0385-5414 https://pubs.kist.re.kr/handle/201004/142741 A synthesis of new trifluoromethylated dihydro-1,4-oxathiin-3-carboxanilids (2) through polymer-bound activated ester is described. Chlorination of ethyl gamma,gamma,gamma-trifluoroacetoacetate (3) followed by treatment of 2-mercaptoethanol gave hydroxyoxathianes isomers (cis-10 and trans-11). Replacement of hydroxy to chlorine and then dehydrochlorination afforded trifluoromethyl dihydro-1,4-oxathiin ester (7). The polymer-bound trifluoromethylated dihydro-1,4-oxathiin-3-carboxylic acid, 4-hydroxy-3-nitrobenzophenone ester (16) was prepared through the reaction of polystyrene-bound 4-hydroxy-3-nitrobenzophenone (14) with the trifluoromethylated dihydro-1,4-oxathiin-3-carbonyl chloride (15). Refluxing of 16 with anilines in acetonitrile gave the corresponding carboxanilide (2). The reaction rate depended on the nucelophilicity of nitrogen in aniline. English PERGAMON-ELSEVIER SCIENCE LTD Synthesis of trifluoromethylated dihydro-1,4-oxathin-3-carboxanilides through polymer-bound activated ester Article 10.3987/COM-98-8290 1 HETEROCYCLES, v.48, no.11, pp.2253 - 2261 HETEROCYCLES 48 11 2253 2261 scie scopus 000077403000005 2-s2.0-0000077631 Chemistry, Organic Chemistry Article