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Synthesis 2016; 48(23): 4207-4212
DOI: 10.1055/s-0035-1562533
DOI: 10.1055/s-0035-1562533
paper
Unified Approach to Pyrazole-Fused Heterocyclic and Carbocyclic Motifs through One-Pot Condensation and Intramolecular Dipolar Cycloaddition Reaction
Further Information
Publication History
Received: 30 May 2016
Accepted after revision: 15 July 2016
Publication Date:
01 September 2016 (online)
Abstract
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.
Key words
intramolecular dipolar cycloaddition - pyrazoles - tosyl hydrazones - diazo compounds - alkynesSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1562533.
- Supporting Information
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Compounds 6a and 6b were prepared from 5-hexyn-1-ol through Sonogashira coupling and oxidation, see: