Journal
SYNTHESIS-STUTTGART
Volume 48, Issue 23, Pages 4207-4212Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0035-1562533
Keywords
intramolecular dipolar cycloaddition; pyrazoles; tosyl hydrazones; diazo compounds; alkynes
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Funding
- Science and Engineering Research Board (SERB), Department of Science and Technology (DST), India [CS-179/2013]
- Council of Scientific Industrial Research (CSIR), India [CSC-0301]
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A one-pot synthesis of highly substituted pyrazoles that are fused to dihydrochromenes, dihydroquinolines and cyclopentane motifs, from readily available precursors is reported. The reaction involves conversion of alkyne-tethered aldehydes into the corresponding tosylhydrazones, base-mediated generation of diazo compounds, and subsequent intramolecular dipolar cycloaddition reaction. A range of internal and terminal alkynes as well as bromoalkyne compounds can be employed as the tethered dipolarophile to afford the corresponding cycloadducts.
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