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Synthesis of furo[2,3-c]-2,7-naphthyridine derivatives via domino heterocyclization reaction

Tetrahedron , 2005, 61 (40), 9618-9623

DOI: 10.1016/j.tet.2005.07.074

Tverdokhlebov A. V.; Zavada A. V.; Tolmachev A. A.; Kostyuk A. N.; Chernega A. N.; Rusanov E. B.

2-Amino-4-cyanomethyl-6-dialkylamino-3,5-pyridinedicarbonitriles were found to react with substituted oxiranes yielding 5,6-diamino-8-dialkylamino-1,2-dihydrofuro[2,3-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-furo[2,3-c]pyrimido[4,5,6-ij]-2,7-naphthyridine-1-carbonitriles and 2-dialkylamino-5,6,9,10-tetrahydro-4H-spiro{furo[2,3-c]pyrimido[4,5,6-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.

Synthesis of furo[2,3-c]-2,7-naphthyridine derivatives via domino heterocyclization reaction

Tverdokhlebov A. V.; Zavada A. V.; Tolmachev A. A.; Kostyuk A. N.; Chernega A. N.; Rusanov E. B.
Tetrahedron 2005, 61 (40), 9618-9623
DOI: 10.1016/j.tet.2005.07.074

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