N-Formylation of amines using arylhydrazones of malononitrile and a Cu(II) complex under eco-friendly conditions at room temperature

[Display omitted] •N-Formylation of amines using arylhydrazones of malononitrile.•The reaction can be performed under solvent-free conditions at room temperature.•The products were obtained in excellent yields without of column chromatography. In this work, we report the synthesis of formamides via...

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Published inInorganica Chimica Acta Vol. 513; p. 119938
Main Authors Nasrollahzadeh, Mahmoud, Bidgoli, Nayyereh Sadat Soheili, Rocha, Bruno G.M., Pombeiro, Armando J.L., Mahmudov, Kamran T.
Format Journal Article
LanguageEnglish
Published Amsterdam Elsevier B.V 01.12.2020
Elsevier Science Ltd
Subjects
Aliphatic amines
Amines
Arylhydrazones of malononitrile
Benzoic acid
Catalysts
Column chromatography
Copper
Formamides
Malononitrile
N-Formylation
Room temperature
Solvent-free
Solvents
Substrates
Arylhydrazones of malononitrile
Amines
N-Formylation
Formamides
Copper
Solvent-free
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Summary:[Display omitted] •N-Formylation of amines using arylhydrazones of malononitrile.•The reaction can be performed under solvent-free conditions at room temperature.•The products were obtained in excellent yields without of column chromatography. In this work, we report the synthesis of formamides via solvent free N-formylation of amines using known arylhydrazones of malononitrile including sodium 2-(2-(dicyanomethylene)hydrazinyl)benzenesulfonate (I), 2-(2-(dicyanomethylene)hydrazinyl) benzoic acid (II) and its Cu(II) complex (III) as catalysts at room temperature. These catalysts are highly active and the scope of the method was investigated using several heterocyclic, aromatic and aliphatic amines as substrates, which produced the corresponding formamides in high yields. The remarkable advantages of this method are the elimination of toxic solvents, operational simplicity, easy workup procedure, excellent yields and avoidance of column chromatography.
ISSN:0020-1693
1873-3255
DOI:10.1016/j.ica.2020.119938