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Abstract Synthesis and discussion of compound (III): The condensed thiopyrano compound 3- amino-7-methyl-1-thioxo-5,6,7,8-tetrahydro-1H-thiopyrano[3,4-c]pyridine-4-carbonitrile (II) was synthesized in high yields via one-step condensation of 1-methylpiperidin-4-one with malononitrile and CS2 in triethyl amine presence to give the thiopyrano Composition (II) which react with morpholine in rearrangement reaction to produce 3-mercapto-7- methyl-1-morpholino-5,6,7,8-tetrahydro-2,7-naphthyridine-4-carbonitrile (III). Scheme 1. 3-mercapto-7-methyl-1-morpholino-5,6,7,8-tetrahydro-2,7-naphthyridine-4-carbonitrile (III) reacted to α-halogenated carbonyl compounds with sodium acetate refluxing ethanol to give s- alkylated mercapto compounds (IVa-i) that were cyclicated by Thorpe-Ziegler to tetrahydrothieno[2,3-c][2,7]-naphthyridino compounds (V a-i) upon heat in ethanol and sodium ethoxide. Compounds (V a-i) can be obtained directly from (III) by refluxation in the presence of potassium carbonate with α-halogenated carbonyl compounds (Scheme 2). Scheme 3. |