73773-25-8Relevant academic research and scientific papers
Electrospray ionization mass spectrometry reveals an unexpected coupling product in the copper-promoted synthesis of pyrazoles
Hyvl, Jakub,Agrawal, Divya,Pohl, Radek,Suri, Mamta,Glorius, Frank,Schroeder, Detlef
, p. 807 - 816 (2013)
The reaction mechanism of the intermolecular oxidative formation of pyrazole 2 via a C-C/N-N bond-formation cascade of the enaminone 1 is investigated by means of ESI-MS. No direct reaction intermediates are observed; however, the formation of an unexpected imidazolid-3-one derivative X is observed that involves an oxidative dimerization of 1 in the presence of dioxygen. The derivative X is isolated and characterized by means of multidimensional 1H and 13C NMR spectroscopy.
PYRAZOLE SYNTHESIS BY COUPLING OF CARBOXYLIC ACID DERIVATIVES AND ENAMINES
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Paragraph 0134, (2013/08/15)
A method of synthesizing Pyrazoles by means of the oxidative conversion of Enamines with suitable N-containing carboxylic acid derivatives in the presence of copper ions and 2-picolinic acid derivatives is provided.
An efficient copper-catalyzed formation of highly substituted pyrazoles using molecular oxygen as the oxidant
Suri, Mamta,Jousseaume, Thierry,Neumann, Julia J.,Glorius, Frank
supporting information; experimental part, p. 2193 - 2196 (2012/09/21)
An efficient Cu-catalyzed formation of tetra-substituted pyrazoles is reported. In this atom economic process, readily available enamines and nitriles are reacted by C-C and N-N bond formation. Oxygen has been successfully used as the oxidant, which has i
Efficient synthesis of pyrazoles: Oxidative C-C/N-N bond-formation cascade
Neumann, Julia J.,Suri, Mamta,Glorius, Frank
supporting information; experimental part, p. 7790 - 7794 (2011/01/09)
Golden section: A novel synthetic strategy for the synthesis of tetrasubstituted pyrazoles is provided. In an efficient C-C/N-N bond-formation cascade, enamines and nitriles are oxidatively coupled to deliver pyrazoles in good yields (see scheme). The rea
Study of the Reaction of 2-(1-Alkoxyalkylidene)-1,3-dicarbonyl Compounds with Hydrazines
Emelina,Iz''yurov,Ermakov,Ershov
, p. 430 - 434 (2007/10/03)
13C NMR study has shown that the only site of primary attack by hydrazines on alkyl 3-oxobutanoates containing an alkoxymethylene or 1-alkoxyethylidene group in position 2 is the ethylenic carbon atom and that the corresponding enehydrazine is the only observable intermediate product. According to quantum-chemical calculations of the electronic structure of the substrates, the reaction is orbital-controlled.
1,3-Dipolar Cycloadditions, 88. C-Methyl-N-phenylnitrilimine and the Regiochemistry of its Cycloadditions
Fliege, Werner,Huisgen, Rolf,Clovis, James S.,Knupfer, Hans
, p. 3039 - 3061 (2007/10/02)
The title compound, a representative of the little known C-alkylnitrilimines, is accessible by three routes: NaNO2 elimination from sodium (α-nitroethylidene)phenylhydrazine in boiling acetonitrile, photolysis of 5-methyl-2-phenyltetrazole, and the thermo
