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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- 作者：Tverdokhlebov ; Anton V. ; Resnyanska ; Elizaveta V. ; Zavada ; Alexander V. ; Tolmachev ; Andrey A. ; et. al.
- 关键词：Cascade reactions ; Nitriles ; Chloroacetamides ; Pyrrolo[2 ; 3-c]2 ; 7-naphthyridines ; Spiro compounds
- 刊名：Tetrahedron
- 出版年：2004
- 出版时间：June 28, 2004
- 年：2004
- 卷：60
- 期：27
- 页码：5777-5783
- 全文大小：204 K
文摘
Alkylation of the title pyridinedicarbonitriles with N-substituted chloroacetamides was found to give 5,6-diamino-8-dialkylamino-2,3-dihydro-2-oxo-1H-pyrrolo[2,3-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-oxopyrimido[4,5,6-ij]pyrrolo[2,3-c]2,7-naphthyridine-1-carbonitriles and 2-dialkylamino-4,5,6,8,9,10-hexahydro-9-oxospiro{pyrimido[4,5,6-ij]pyrrolo[2,3-c]2,7-naphthyridine-5,1′-cyclohexane}-1-carbonitriles, respectively. All fused 2,7-naphthyridines obtained were derivatives of novel heterocyclic systems.