Synthesis of furo[2,3-c]-2,7-naphthyridine derivatives via domino heterocyclization reaction |
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Authors: | Anton V Tverdokhlebov Alexander V Zavada Alexander N Kostyuk Eduard B Rusanov |
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Institution: | a Enamine Ltd Co., Alexandra Matrosova str. 23, 01103, Kiev, Ukraine b Chernigov State University of Technology, Shevchenko str. 95, 14027 Chernigov, Ukraine c Kiev National Taras Shevchenko University, Volodimirska str. 62, 01033 Kiev, Ukraine d Institute of Organic Chemistry NAS, Murmanska str. 5, 02094 Kiev, Ukraine |
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Abstract: | 2-Amino-4-cyanomethyl-6-dialkylamino-3,5-pyridinedicarbonitriles were found to react with substituted oxiranes yielding 5,6-diamino-8-dialkylamino-1,2-dihydrofuro2,3-c]-2,7-naphthyridine-9-carbonitriles. The oxirane ring was shown to be opened selectively from the unsubstituted side and further cyclization occurred with participation of 3-CN, but not 5-CN of the starting pyridines. The furonaphthyridines obtained were converted into 2-dialkylamino-5-methyl-9,10-dihydro-4H-furo2,3-c]pyrimido4,5,6-ij]-2,7-naphthyridine-1-carbonitriles and 2-dialkylamino-5,6,9,10-tetrahydro-4H-spiro{furo2,3-c]pyrimido4,5,6-ij]-2,7-naphthyridine-5,1′-cyclohexane}-1-carbonitriles by treatment with acetic anhydride and cyclohexanone, respectively. The structure of prepared compounds was confirmed unambiguously by X-ray crystallographic study. |
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Keywords: | Domino reactions Furo[2 3-c]-2 7-naphthyridines Nitriles Oxiranes Spiro compounds |
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