Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 81, Issue 22, Pages 11072-11080Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b02076
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Funding
- Priority Academic Program Development (PAPD) of Jiangsu Higher Education Institutions
- NSFC of Jiangsu China [BK20150315, NSFC21602148]
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A general and transition-metal-free access to the fused polycyclic pyrazoles via an intramolecular 1,3-dipolar cycloaddition reaction of alkyne-tethered tosylhydrazones has been reported. The pure solid products could be obtained without column chromatography in high to excellent yields, and the obtained products are useful bioactive molecules or could be used as the key intermediate for synthesis of these compounds in one or two steps. Additionally, a [3+2]-cycloaddition followed by a direct H shift aromatization reaction mechanism was proposed, which is different from the previously reported aryl or alkyl sequential [1,5]-sigmatropic rearrangement pathway.
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