Synthesis and chemical reactivity of novel pyrano[3,2-c]quinoline-3-carbonitriles
Ibrahim, M.A.; Al-Shimaa Badran;
Abstract
Reaction of 6-methyl-4,5-dioxo-5,6-dihydro-4H-pyrano[3,2-c]quinoline-3-carboxaldehyde (1) with hydroxylamine hydrochloride under different reaction conditions produced a novel pyrano[3,2-c]quinoline derivatvies 2-5. Ring opening ring closure reactions of pyrano[3,2-c]quinoline-3-carbonitrile 2 with some nitrogen nucleophiles afforded the novel 3-heteroaryl-4-hydroxyquinolines. While, treatment of carbonitrile 3 with some nitrogen nucleohilic reagents produced a diversity of annulated pyrano[3,2-c]quinolines. The chemical reactivity of the prepared pyrano[3,2-c]quinoline-3-carbonitriles 2 and 3 is widely different depending on the different reactivity of pyran-2-one and pyran-4-one moieties toward the nucleophilic reagents as well as the functional groups present in pyrone rings
Other data
Title | Synthesis and chemical reactivity of novel pyrano[3,2-c]quinoline-3-carbonitriles | Authors | Ibrahim, M.A.; Al-Shimaa Badran | Keywords | 4-hydroxyquinolin-2(1H)-one;Annulated pyrano[3,2-c]quinoline;pyrano[3,2-c]quinoline-3-carbonitrile;pyrimidines;RORC | Issue Date | 2020 | Publisher | Taylor & Francis Group | Journal | Synthetic Communications | Volume | 50 | Start page | 1871 | End page | 1882 | DOI | 10.1080/00397911.2020.1759095 |
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