Effect of specific solute-solvent interaction and electron donor-acceptor substituents of novel pyrazolo naphthyridines on fluorescence.
Heterocyclic orthoaminoaldehyde such as 4-amino-3-(4-phenyl)-1-phenyl-1H-Pyrazolo[3,4-b]pyridine-5-carbaldehyde was synthesized by multistep reactions involving reduction of azido derivative 2 with LAH to yield aminoalcohol 3 and oxidation of it with MnO(2) to aminoaldehyde 4.The pyridine ring annulated on to 4 by Friedländer condensation using acetophenones in presence of base to obtained pyrazolo[3,4-h][1,6]naphthyridine 5 in excellent yield. Study of photophysical properties of 5 revealed that the absorption and emission of them depends up on the substituents present on benzene ring in newly annulated pyridine ring.
Patil
Sandeep R
SR
Organic Chemistry Research Centre, Department of Chemistry, KTHM College, Nashik, MS, India.
Shelar
Deepak P
DP
Rote
Ramhari V
RV
Toche
Raghunath B
RB
Jachak
Madhukar N
MN
D004583:Electrons; D005453:Fluorescence; D009682:Magnetic Resonance Spectroscopy; D009287:Naphthyridines / Q000737:chemistry*; D011720:Pyrazoles / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry*; D013055:Spectrophotometry, Infrared
D009287:Naphthyridines; D011720:Pyrazoles; D012997:Solvents