1. Efficient construction of pyrazolo[1,5-a]pyrimidine scaffold and its exploration as a new heterocyclic fluorescent platform.
- Author
-
Wu YC, Li HJ, Liu L, Wang D, Yang HZ, and Chen YJ
- Subjects
- Binding, Competitive, Molecular Structure, Pyrimidines chemistry, Spectrometry, Fluorescence, Structure-Activity Relationship, Fluorescent Dyes chemical synthesis, Fluorescent Dyes chemistry, Pyrazoles chemistry, Pyrimidines chemical synthesis
- 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.
- Published
- 2008
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