37612-61-6Relevant articles and documents
Enantio- and Site-Selective α-Fluorination of N-Acyl 3,5-Dimethylpyrazoles Catalyzed by Chiral π–CuII Complexes
Ishihara, Kazuaki,Nishimura, Kazuki,Yamakawa, Katsuya
supporting information, p. 17641 - 17647 (2020/08/14)
Catalytic enantioselective α-fluorination reactions of carbonyl compounds are among the most powerful and efficient synthetic methods for constructing optically active α-fluorinated carbonyl compounds. Nevertheless, α-fluorination of α-nonbranched carboxylic acid derivatives is still a big challenge because of relatively high pKa values of their α-hydrogen atoms and difficulty of subsequent synthetic transformation without epimerization. Herein we show that chiral copper(II) complexes of 3-(2-naphthyl)-l-alanine-derived amides are highly effective catalysts for the enantio- and site-selective α-fluorination of N-(α-arylacetyl) and N-(α-alkylacetyl) 3,5-dimethylpyrazoles. The substrate scope of the transformation is very broad (25 examples including a quaternary α-fluorinated α-amino acid derivative). α-Fluorinated products were converted into the corresponding esters, secondary amides, tertiary amides, ketones, and alcohols with almost no epimerization in high yield.
Copper-catalyzed C–N cross-coupling of arylboronic acids with N-acylpyrazoles
Zhang, Jin,Jia, Run-Ping,Wang, Dong-Hui
supporting information, p. 3604 - 3607 (2016/07/21)
A copper-catalyzed C–N bond forming reaction of arylboronic acids and N-acylpyrazoles was developed. This procedure used N-acetyl protected pyrazoles as starting material instead of free pyrazoles (NH). The reaction worked under neutral conditions and did not require any base or ligand. The reaction showed good functional group tolerance.
Ring-ring tautomerism in 1,3-alkanoylhydrazonoximes of acetylacetone
Ershov,Dobrodumov
, p. 722 - 727 (2007/10/03)
The coexistence in solution of tautomeric isoxazoline and pyrazoline forms of 1,3-alkanoylhydrazonoxime of acetylacetone has been detected and investigated by 1H and 13C NMR spectroscopic methods. The compounds indicated eliminate hydroxylamine under the action of acid catalysts, forming 1-acyl-3,5-dimethylpyrazoles.