Journal
JOURNAL OF COMBINATORIAL CHEMISTRY
Volume 12, Issue 1, Pages 31-34Publisher
AMER CHEMICAL SOC
DOI: 10.1021/cc9001179
Keywords
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Funding
- National Natural Sciences Foundation of China [20772103]
- Natural Science Foundation in Jiangsu Province [BK2007028]
- Qin Lan Project in Jiangsu Province [QL200607, 08QLT001]
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The silica get-catalyzed synthesis of 5-amino-2-aryl-3H-chromeno[4,3,2-de][1,6]naphthyridine-4-carbonitriles and 5-amino-2-aryl-3H-quinolino[4,3,2-de][1,6]naphthyidine-4-carbonitriles were simply achieved upon the one-pot cascade reaction of malononitrile with Substituted 2-hydroxyacetophenone (or 2-aminoacetophenone) and aromatic aldehyde in aqueous media. The mechanistic investigation results based on electrospray ionization mass spectrometry (ESI-MS) indicated that malononitrile displayed a dual role during this transformation. Thirteen bonds were cleaved and 12 new bonds were constructed in the formation of 5-amino2-aryl-3H-chromeno[4,3,2-de][1,6]naphthyridine-4-carbonitriles, while only 2 H2O molecules were removed. The fluorescence properties screening showed five new compounds have high fluorescence quantum yields.
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