Journal
TETRAHEDRON
Volume 74, Issue 30, Pages 4119-4125Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2018.06.027
Keywords
Pyrano[3,2-c]quinoline-3-carbonitrile; Pyridopyranoquinolines; RORC; Nucleophilic reactions; Cycloaddition; Heterocyclization
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A variety of novel heteroannulated pyrano[3,2-c]quinolines 2-12 was efficiently synthesized via a domino 'Michael/retro-Michael/nitrile addition/heterocyclization' reactions between 6-ethyl-5,6-dihydro-4,5-dioxo-4H-pyrano[3,2-cjquinoline-3-carbonitrile (1) and a diversity of carbon nucleophilic reagents. Pyrido[3',2':5,6]pyrano[3,2-c]quinolines 2-6 were synthesized from ring opening ring closure reactions of carbonitrile 1 with some methylene active nitrile namely malononitrile, cyanoacetamide, N-phenylcyanoacetamide, (phenylthio)acetonitrile and ethyl cyanoacetate, respectively. Reactions of carbonitrile I with dimer malononitrile and cyanoacetohydrazide showed different behavior producing the novel heteroannulated pyranoquinoline derivatives 7 and 8, respectively. Treatment of carbonitrile 1 with some methylene active ketones namely acetylacetone, acetoacetanilide, ethyl acetoacetate and ethyl benzoylacetate afforded pyrido[3',2':5,6]pyrano[3,2-c]quinolines 9-12, respectively. Structures of the synthesized products were deduced on the basis of their analytical and spectral data. (C) 2018 Elsevier Ltd. All rights reserved.
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