Synthesis of pyrrolo[2,3-c]2,7-naphthyridine derivatives by cascade heterocyclization reaction of 2-amino-4-cyanomethyl-6-dialkylamino-3,5-pyridinedicarbonitriles |
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Authors: | Anton V Tverdokhlebov Elizaveta V Resnyanska Andrey A Tolmachev Alexander N Chernega |
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Institution: | a Enamine Ltd. Co., I. Kudri str. 31, apt. 17, 02042 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, Murmanskaya str. 5, 02094 Kiev, Ukraine |
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Abstract: | Alkylation of the title pyridinedicarbonitriles with N-substituted chloroacetamides was found to give 5,6-diamino-8-dialkylamino-2,3-dihydro-2-oxo-1H-pyrrolo2,3-c]2,7-naphthyridine-9-carbonitriles. The structure of obtained compounds was unambiguously confirmed by X-ray crystallographic study. The heterocyclization reaction proceeded regioselectively involving 3-CN group of the starting pyridines without participation of 5-CN. The reasons of the selectivity were discussed. An interaction of prepared naphthyridine derivatives with acetic acid anhydride and cyclohexanone yielded 2-dialkylamino-6,8,9,10-tetrahydro-5-methyl-9-oxopyrimido4,5,6-ij]pyrrolo2,3-c]2,7-naphthyridine-1-carbonitriles and 2-dialkylamino-4,5,6,8,9,10-hexahydro-9-oxospiro{pyrimido4,5,6-ij]pyrrolo2,3-c]2,7-naphthyridine-5,1′-cyclohexane}-1-carbonitriles, respectively. All fused 2,7-naphthyridines obtained were derivatives of novel heterocyclic systems. |
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Keywords: | Cascade reactions Nitriles Chloroacetamides Pyrrolo[2 3-c]2 7-naphthyridines Spiro compounds |
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