Metal‐Free Synthesis of Pyrazoles from 1,3‐Diarylpropenes and Hydrazines via Multiple Inter‐/Intramolecular C–H Aminations

A facile and metal‐free access to pyrazoles from 1,3‐diarylpropenes and hydrazines via multiple inter‐/intramolecular C‐H aminations was described. Under the neutral and mild 2,3‐dichloro‐5,6‐dicyanobenzoquinone (DDQ) oxidative conditions, various disubstituted pyrazoles were synthesized in moderate...

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Bibliographic Details
Published inAdvanced synthesis & catalysis Vol. 359; no. 15; pp. 2610 - 2620
Main Authors Tang, Li, Ma, Minyan, Zhang, Qi, Luo, Huan, Wang, Tao, Chai, Yonghai
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 07.08.2017
Wiley Subscription Services, Inc
Subjects
2,3-dichloro-5,6-dicyanobenzoquinone (DDQ)
cascade reaction
Chemistry
Chemistry, Applied
Chemistry, Organic
Hydrazines
metal-free conditions
multiple C–H aminations
Physical Sciences
pyrazoles
Science & Technology
INTERMOLECULAR AMINATION
2,3-dichloro-5,6-dicyanobenzoquinone (DDQ)
cascade reaction
ONE-POT SYNTHESIS
AMBIENT-TEMPERATURE
TETRASUBSTITUTED PYRAZOLES
multiple C-H aminations
HIGHLY EFFICIENT
metal-free conditions
FACILE ACCESS
REGIOSELECTIVE SYNTHESIS
1,3,5-TRISUBSTITUTED PYRAZOLES
BIOLOGICAL EVALUATION
N BOND FORMATION
pyrazoles
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Summary:A facile and metal‐free access to pyrazoles from 1,3‐diarylpropenes and hydrazines via multiple inter‐/intramolecular C‐H aminations was described. Under the neutral and mild 2,3‐dichloro‐5,6‐dicyanobenzoquinone (DDQ) oxidative conditions, various disubstituted pyrazoles were synthesized in moderate to excellent yields. This method provides a pot‐ and step‐economic strategy for the construction of pyrazoles, especially those for drug discovery.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201700196