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Abstract The compound 3-amino-1-thioxo-5,6,7,8-tetrahydro-1H-isothio chromene-4-carbonitrile (I) was transformed into 5,6,7,8tetrahydroisoquinoline derivative II by using piperidine via Dimorth rearrangement in an excellent yield. Compound II was reacted with various α-halo carbonyl compounds such as: chloroacetone, ethyl chloroacetate, phenacyl bromide, chloro acetamide, and chloro acetanilide in refluxing ethanol and fused sodium acetate to afford the corresponding S-alkylated products IIIa-e, which in turn underwent Thorpe-Ziegler cyclization upon treatment with ethanolic sodium ethoxide solution yielded 1-amino-2-substituted-5-piperidinyl thieno[2,3-c]isoquinolines (IVa-e). The latter compounds were obtained via an alternative route, upon reaction of compound II with the mentioned α-halo carbonyl compounds using anhydrous potassium carbonate as a basic catalyst instead of sodium acetate. |