1,2-Azoles: pyrazoles, isothiazoles and isoxazoles: reactions and synthesis

Joule, J. A.; Mills, K.; Smith, G. F.

doi:10.1007/978-1-4899-3222-8_22

Cited by 3 publications

(1 citation statement)

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“…Application of Claisen condensation of the appropriate alkyl methyl ketone 6 with diethyl oxalate by the use of sodium ethoxide in absolute ethanol afforded the corresponding 2,4-diketoesters 7. The later compounds were reacted with hydrazines in appropriate solvent, and the pyrazole-3-carboxylic acid ethyl esters 8 were formed (Scheme 3) [6,[23][24][25][26][27][28][29][30][31][32].…”

Section: -mentioning

confidence: 99%

Synthetic Routes to Pyrazole‐3(5)‐carboxylates

Khidre

Abdel‐Wahab

Farahat

et al. 2015

Journal of Heterocyclic Chem

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Section: -mentioning

confidence: 99%

Synthetic Routes to Pyrazole‐3(5)‐carboxylates

Khidre

Abdel‐Wahab

Farahat

et al. 2015

Journal of Heterocyclic Chem

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Mild Copper‐Catalyzed Vinylation Reactions of Azoles and Phenols with Vinyl Bromides

Taillefer¹,

Ouali²,

Renard³

et al. 2006

Chemistry A European J

122

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An efficient and straightforward copper-catalyzed method allowing vinylation of N- or O-nucleophiles with di- or trisubstituted vinyl bromides is reported. The procedure is applicable to a broad range of substrates since N-vinylation of mono-, di-, and triazoles as well as O-vinylation of phenol derivatives can be performed with catalytic amounts of copper iodide and inexpensive nitrogen ligands 3 or 8. In the case of more hindered vinyl bromides, the use of the original bidentate chelator 8 was shown to be more efficient to promote the coupling reactions than our key tetradentate ligand 3. The corresponding N-(1-alkenyl)azoles and alkenyl aryl ethers are obtained in high yields and selectivities under very mild temperature conditions (35-110 degrees C for N-vinylation reactions and 50-80 degrees C for O-vinylation reactions). Moreover, to our knowledge, this method is the first example of a copper-catalyzed vinylation of various azoles. Finally, this protocol, practical on a laboratory scale and easily adaptable to an industrial scale, is very competitive compared to the existing methods that allow the synthesis of such compounds.

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