Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 81, Issue 21, Pages 10328-10338Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b01326
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Funding
- Fonds der Chemischen Industrie
- Deutsche Forschungsgemeinschaft [Mu 1088/9-1]
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Consecutive four-component coupling-coupling-cyclocondensation syntheses of pyrazoles and pyrimidines were developed by taking advantage of the provisional, sequentially Pd-catalyzed one-pot generation of alkynones from aryl iodides, ethynylmagnesium bromide, and acid chlorides. This one-pot methodology allows the concise, diversity-oriented generation of a set of donor-, acceptor-, and donor acceptor-substituted pyrazoles, which are interesting fluorophores. Most distinctly, donor acceptor pyrazoles display remarkably red-shifted emission maxima and pronounced positive solvochromicity, spanning an overall range from 363 nm (cyclohexane) to 595 nm (acetonitrile). DFT and TD-DFT calculations elucidate the electronic structure and the photophysical behavior. Upon photonic excitation, considerable charge-transfer character becomes apparent, which rationalizes the origin of huge Stokes shifts and solvochromic behavior.
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