1,3-Dipolar cycloaddition of 3-alkylsulfanyl-2-arylazo-3-(tert-cycloalkylamino)acrylonitriles with N-methyl- and N-phenylmaleimides

A series of 1,2-diaza-1,3-butadienes with terminal S,N-acetal function were obtained and reacted with N-methyl- and N-phenylmaleimides. As a result of the 1,3-dipolar cycloaddition, a range of new functionalized nonaromatic heterocyclic compounds including: octahydro-1H-pyrrolo[3,4-a]indolizine, octahydropyrrolo[3′,4′:3,4]pyrrolo[1,2-a]azepine, hexahydropyrrolo[3′,4′:3,4]pyrrolo[2,1-c][1,4]oxazine and -thiazine, were obtained with good yields in mild conditions. Experimental and theoretic results allowed establishment of a relationship between the structures of the tert-cycloalkylamine group and the activity of the azomethine ylides generated.

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