Silica gel-catalyzed one-pot syntheses in water and fluorescence properties studies 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]naphthyridine-4-carbonitriles.
The silica gel-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]naphthyridine-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-amino-2-aryl-3H-chromeno[4,3,2-de][1,6]naphthyridine-4-carbonitriles, while only 2 H(2)O molecules were removed. The fluorescence properties screening showed five new compounds have high fluorescence quantum yields.
Wu
Hui
H
School of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou, China. wuhui72@yahoo.com.cn
Lin
Wei
W
Wan
Yu
Y
Xin
Hai-qiang
HQ
Shi
Da-qing
DQ
Shi
Yan-hui
YH
Yuan
Rui
R
Bo
Rong-cheng
RC
Yin
Wei
W
D000588:Amines / Q000138:chemical synthesis*; D001578:Benzopyrans / Q000138:chemical synthesis*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D005456:Fluorescent Dyes / Q000138:chemical synthesis*; D005782:Gels / Q000737:chemistry*; D015394:Molecular Structure; D009287:Naphthyridines / Q000138:chemical synthesis*; D009570:Nitriles / Q000138:chemical synthesis* / Q000737:chemistry; D011804:Quinolines / Q000138:chemical synthesis*; D012822:Silicon Dioxide / Q000737:chemistry*; D014867:Water / Q000737:chemistry*
D000588:Amines; D001578:Benzopyrans; D005456:Fluorescent Dyes; D005782:Gels; D009287:Naphthyridines; D009570:Nitriles; D011804:Quinolines; D014867:Water; D012822:Silicon Dioxide; C000945:dicyanmethane