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Efficient Construction of Pyrazolo[1,5-a]pyrimidine Scaffold and its Exploration as a New Heterocyclic Fluorescent Platform
- Source :
- Journal of Fluorescence. 18:357-363
- Publication Year :
- 2007
- Publisher :
- Springer Science and Business Media LLC, 2007.
-
Abstract
- An efficient, fast and facile pyrazolo[1,5-a]pyrimidine synthetic protocol has been established by the condensation of aminopyrazoles with 1,3-dicarbonyl components in AcOH/H(2)SO(4) system. The pyrazolo[1,5-a]pyrimidine sulfides were selectively oxidized to the sulfones via a temperature-controlled stepwise oxidative fashion. The correlation between the substitution patterns of these pyrazolo[1,5-a]pyrimidines and their fluorescent spectroscopic properties were further examined, which provided the fundamentals for their potential applications in the development of new fluorescent probes. Red-shifts were easily achieved by the incorporation of unsaturated groups at the 5- and 7-positions, which suggested an approach for synthesizing long wavelength pyrazolo[1,5-a]pyrimidine dyes. The fluorescent spectroscopic properties were found to be sensitive to the hydroxy-containing and carbonyl-containing media such as alcohol and acetone, which helps to confirm the promising perspectives of further investigations in this area.
- Subjects :
- Scaffold
Fluorophore
Molecular Structure
Sociology and Political Science
Pyrimidine
Clinical Biochemistry
Binding, Competitive
Biochemistry
Fluorescence
Structure-Activity Relationship
Clinical Psychology
chemistry.chemical_compound
Long wavelength
Pyrimidines
Spectrometry, Fluorescence
chemistry
Acetone
Pyrazoles
Organic chemistry
Law
Spectroscopy
Social Sciences (miscellaneous)
Fluorescent Dyes
Subjects
Details
- ISSN :
- 15734994 and 10530509
- Volume :
- 18
- Database :
- OpenAIRE
- Journal :
- Journal of Fluorescence
- Accession number :
- edsair.doi.dedup.....74f81d7658ee297131543988c91bb199