Regioselective Synthesis of 4-Nitro- or 4-Chloro-Tetrasubstituted Pyrazoles from Hydrazones and [beta]-Halo-[beta]-nitrostyrenes

Regioselective Synthesis of 4-Nitro- or 4-Chloro-Tetrasubstituted Pyrazoles from Hydrazones and [beta]-Halo-[beta]-nitrostyrenes

We report an acid-catalyzed cycloaddition reaction of hydrazones with [beta]-bromo- or [beta]-chloro-[beta]-nitrostyrenes for the regioselective synthesis of 4-nitro- or 4-chloro-tetrasubstituted pyrazoles. Arising from a common 4-halo-4-nitropyrazolidine intermediate, the identity of the pyrazole p...

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Veröffentlicht in:European journal of organic chemistry 2014-01, Vol.2014 (2), p.410
Hauptverfasser: Deng, Xiaohu, Liang, Jimmy T, Mani, Neelakandha S
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container_title European journal of organic chemistry
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Liang, Jimmy T
Mani, Neelakandha S
description We report an acid-catalyzed cycloaddition reaction of hydrazones with [beta]-bromo- or [beta]-chloro-[beta]-nitrostyrenes for the regioselective synthesis of 4-nitro- or 4-chloro-tetrasubstituted pyrazoles. Arising from a common 4-halo-4-nitropyrazolidine intermediate, the identity of the pyrazole product formed is dependent on the relative leaving group abilities of the halo and nitro substituents.
doi_str_mv 10.1002/ejoc.201301294
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title Regioselective Synthesis of 4-Nitro- or 4-Chloro-Tetrasubstituted Pyrazoles from Hydrazones and [beta]-Halo-[beta]-nitrostyrenes
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