Synthese heterocyclisch substituierter 4-Piperidinyl-1,4-dihydropyridine durch Ringschlußreaktion an einer N-Acylthioamid- und N-Acylisothioamid-Seitenkette

Synthesis of Heterocyclically Substituted-4-Piperidinyl-1,4-dihydropyridines by Ring Closure Reactions at a N-Acylthioamide- or at a N-Acylisothioamide-Side-Group A series of 4-(2′-methylenepiperidin-4′-yl)-1,4-dihydropyridines 5–7 and 9–11 ] with a heterocyclic substituent at the methylene group is prepared by reaction of the nonsubstituted compound 1 with benzoylisothiocyanate or ethoxycarbonylisothiocyanate to the N-benzoylthioamide 2 or the N-ethoxycarbonylthioamide 3 , transformation of 2 into the isothioamide 4 by S-methylation, and subsequent ring closure of 2, 3 or 4 with hydrazine, methylhydrazine, phenylhydrazine, 1,2-diaminoethane, 1,2- and 1,3-diaminopropane, o-diaminobenzene and o-aminophenol.