Reactions of 3-alkylsulfanyl-2-arylazo-3-(1-azacycloalk-1-yl)acrylonitriles with maleimide |
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Authors: | Belskaya N P Koksharov A V Deryabina T G Eltsov O S Slepukhin P A Bakulev V A |
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Institution: | 1.First Russian President B. N. El’tsin Ural State Technical University, 19 ul. Mira, 620002, Ekaterinburg, Russian Federation ;2.I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 20 ul. S. Kovalevskoi, 620041, Ekaterinburg, Russian Federation ; |
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Abstract: | Reactions of 2-arylazo-3-(1-azacycloalk-1-yl)-3-methylsulfanylacrylonitriles with male-imide in benzene gave octahydropyrrolo3,4-a]pyrrolizines 2a–c, decahydro-2,7a-diaza-cyclopentaa]indene 2e, and decahydro-5-oxa-2,7a-diazacyclopentaa]indene 2f as a result of 1,3-dipolar cycloaddition. In a similar reaction with 3-allylsulfanyl-2-arylazo-3-(1-azacycloalk-1-yl)acrylonitriles
3, dipolar cycloaddition and intramolecular cyclization competed to give a mixture of compounds 2 (major products) and 1,4,6,7,8,8a-hexahydropyrrolo2,1-c]-1,2,4-triazines 4b–d, 1,6,7,8,9,9a-hexahydro-4H-pyrido2,1-c]-1,2,4-triazine 4e, and 1,4,6,7,9,9a-hexahydro-1,4-oxazino3,4-c]-1,2,4-triazine 4f (minor products). |
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