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 annula...

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Bibliographic Details
Published in:Journal of fluorescence 2011, Vol.21 (1), p.461-471
Main Authors: Patil, Sandeep R., Shelar, Deepak P., Rote, Ramhari V., Toche, Raghunath B., Jachak, Madhukar N.
Format: Article
Language:English
Subjects:
Acetophenone
Analytical Chemistry
Benzene
Biochemistry
Biological and Medical Physics
Biomedical and Life Sciences
Biomedicine
Biophysics
Biotechnology
Condensing
Derivatives
Electrons
Emission analysis
Fluorescence
Magnetic Resonance Spectroscopy
Naphthyridines - chemistry
Pyrazoles - chemistry
Pyridines
Rapid Communication
Reduction
Solvents - chemistry
Spectrophotometry, Infrared
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Summary: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.
ISSN:1053-0509
1573-4994
DOI:10.1007/s10895-010-0707-0