Metal-free cyclization of unsaturated hydrazones for the divergent assembly of pyrazolones and pyrazolines

An oxidative cyclization of ,-unsaturated hydrazones for the divergent assembly of pyrazolones and pyrazolines under metal-free conditions is presented. This divergent synthetic strategy was achieved by controlling the reaction atmosphere. A number of pyrazolines were obtained via 5- exo -trig cycli...

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Published inChemical communications (Cambridge, England) Vol. 55; no. 61; pp. 8943 - 8946
Main Authors Liu, Xiaobing, Zhou, Yao, Song, Qiuling
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 07.08.2019
Royal Society of Chemistry
Subjects
Assembly
chemical bonding
chemical reactions
Chemistry
Chemistry, Multidisciplinary
Crystallography
Hydrazones
nitrogen
oxygen
Physical Sciences
Pyrazolones
Science & Technology
N-RADICALS
STRATEGY
CONSTRUCTION
BONDS
CASCADE
GENERATION
HYDROAMINATION
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Summary:An oxidative cyclization of ,-unsaturated hydrazones for the divergent assembly of pyrazolones and pyrazolines under metal-free conditions is presented. This divergent synthetic strategy was achieved by controlling the reaction atmosphere. A number of pyrazolines were obtained via 5- exo -trig cyclization when the reaction was performed under N 2 . Whereas when the reaction was conducted under O 2 , diverse functionalized pyrazolones were achieved via oxidative cleavage of the C&z.dbd;C double bond. An oxidative cyclization of ,-unsaturated hydrazones for the divergent assembly of pyrazolones and pyrazolines under metal-free conditions is presented.
Bibliography:Electronic supplementary information (ESI) available. CCDC
1876777
2c
For ESI and crystallographic data in CIF or other electronic format see DOI
3f
1916783
2f
and
(
10.1039/c9cc04039k
)
1916788
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SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1359-7345
1364-548X
1364-548X
DOI:10.1039/c9cc04039k