One-pot synthesis of highly functionalized stable ketenimines of 2,2,2-trifluoro-N-aryl-acetamides

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Reaction of cyclohexyl isocyanide with aromatic aldehydes, aniline derivatives and trifluoroacetic anhydride in dichloromethane at room temperature afforded N-[cyclohexylcarbamoyl(aryl)methyl]-2,2,2-trifluoro-N-arylacetamide derivatives in nearly quantitative yields after 10 min. The work-up procedure is very easy and the products are precipitated in ether as pure solids. The structure of one of the products was established by X-ray single crystal analysis.

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confidence: 83%

Four-Component Reaction between Cyclohexyl Isocyanide, Aromatic Aldehydes, Aromatic Amines and Trifluoroacetic Anhydride

Anary‐Abbasinejad

Anaraki‐Ardakani

Rasekh

et al. 2010

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“…The reaction of aromatic amines with squaric acid in boiling water has also been reported for the preparation of squaramic acids. 14 In continuation of our previous work on isocyanide-based multi-component reactions, 15,16 we now report a facile approach to the synthesis of squaramic acids, together with symmetric and asymmetric squaryl diamides by the reaction of squaric acid with alkyl isocyanides. * Correspondent.…”

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confidence: 85%

The Formation of Squaramic Acids and Squaryl Diamides by the Reaction of Squaric Acid with Alkyl Isocyanides

Mehrabi

Anary‐Abbasinejad

Pour

2013

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The reaction between squaric acid with one equivalent of alkyl isocyanides such as t-butyl isocyanide, cyclohexyl isocyanide and n-butyl isocyanide in ethanol at room temperature after 3h afforded the corresponding squaramic acid derivatives. Symmetric 2,4-squaryl diamides were obtained when the reaction of squaric acid was carried out with two equivalents of alkyl isocyanides under the same conditions. Asymmetric 2,4-squaryl diamides were obtained by reaction of squaramic acids with one equivalent of alkyl isocyanides.Keywords: squaric acid, squaramic acid, symmetric and asymmetric squaryl diamides 1676, 1603, 1536, 1484, 1218 cm −1 , 1 H NMR (500 MHz, d6-DMSO): δ = 0.84-1.46 (7H, m, n-butyl), 1.23 (9H, s, t-butyl), 2.75 (2H, t, J = 7.3 Hz), 5.51 and 7.99 (2 H, D 2 O-exchangeable OH and NH) ppm. 13 C NMR (125 MHz, d6-DMSO): δ =

“…10,11 The reaction of 1-azadienes with various chiral dienophiles, which leads to substituted pyridines, has been reported. 12,13 In the course of our work on the reaction between isocyanides and acetylenic esters, [14][15][16][17] we now report an efficient synthetic route to 1-azadienes and stable ketenimines using alkyl isocyanides 1, dialkyl acetylenedicarboxylates 2, and theophylline derivatives as strong NH-acids (Scheme 1).…”

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confidence: 98%

Synthesis of Highly Functionalised 1-Azadienes and Ketenimines by the Reaction of Alkyl Isocyanides and Dialkyl Acetylenedicarboxylates in the Presence of Theophylline Derivatives

Mosslemin

Shams

Anaraki‐Ardakani

et al. 2013

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