Stereoselective synthesis and alkylation of N-methylmorpholinium 4,5-trans-4-(2-chlorophenyl)-3-cyano-6-hydroxy- 5-(2-thenoyl)-6-trifluoromethyl- 1,4,5,6-tetrahydropyridine-2-thiolate. Molecular and crystal structure of 4,5-trans-4-(2-chlorophenyl)-3-cyano- 6-hydroxy-2-methallylthio-5-(2-thenoyl)- 6-trifluoromethyl-1,4,5,6-tetrahydropyridine

Article abstract of DOI:10.1023/A:1013889208646

The condensation of 2-chlorobenzaldehyde with cyanothioacetamide and 2-thenoyltrifluoroacetone in the presence of N-methylmorpholine takes place stereoselectively and leads to the formation of N-methylmorpholinium 4,5-trans-4-(2-chlorophenyl)-3-cyano-6-hydroxy-5-(2-thenoyl) -6-trifluoromethyl-1,4,5,6-tetrahydropyridine-2-thiolate. The latter was used to synthesize the corresponding 2-alkylthiotetrahydropyridines. The structure of 4,5-trans-4-(2-chlorophenyl)-3-cyano-6-hydroxy-2- methallylthio-5-(2-thenoyl)-6-trifluoromethyl-1,4,5,6-tetrahydropyridine was determined by X-ray crystallographic analysis.