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, oct...

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Bibliographic Details
Published in:Tetrahedron 2015-03, Vol.71 (9), p.1438-1447
Main Authors: Belskaya, Nataliya P., Lesogorova, Svetlana G., Subbotina, Julia O., Koksharov, Aleksandr V., Slepukhin, Pavel A., Dehaen, Wim, Bakulev, Vasiliy A.
Format: Article
Language:English
Subjects:
Azomethine ylide
Cycloaddition
Diazadiene
Maleimide
S,N-Acetal
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Summary: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. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2014.12.087