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A new, one-step method for the synthesis of substituted 3,5-dicyanospiro-4(piperidine-4′)-1H,4H-dihydropyridine-3-thiolates and 2,6-diamino-3,5-dicyanospiro-4-[(piperidine-4′) or (2′ -oxoindole-3′)]-4H-thiopyrans using a multicomponent reaction of N-substituted piperidine-4-ones and isatins with derivatives of cyanoacetic acid is described. The regioselectivity of this reaction can be controlled by varying the substituents at the nitrogen atom of the piperidine-4-ones. The multicomponent reaction of N-alkylpiperidine-4-ones with malononitrile and cyanothioacetamide gives spiro-4-(1′ -alkylpiperidine-4′)-1H,4H-dihydropyridine-2-thiolates, whereas a similar reaction of N-(acyl)alkoxycarbonylpiperidine-4-ones leads exclusively to spiro-4-(1′ -(acyl)alkoxycarbonylpiperidine-4′)-4H-thiopyrans.