Synthesis Of N-sulfonyl Amidines Research Articles

Synthesis of N-sulfonylamidines via three-component reaction of proline, aldehydes, and sulfonyl azides under metal-free conditions

Synthesis of N-sulfonylamidines via three-component reaction of proline, aldehydes, and sulfonyl azides under metal-free conditions

Copper-Catalyzed One-Pot Synthesis of N-Sulfonyl Amidines from Sulfonyl Hydrazine, Terminal Alkynes and Sulfonyl Azides.

N-Sulfonyl amidines are developed from a Cu-catalyzed three-component reaction from sulfonyl hydrazines, terminal alkynes and sulfonyl azides in toluene at room temperature. Particularly, the intermediate N-sulfonylketenimines was generated via a CuAAC/ring-opening procedure and took a nucleophilic addition with the weak nucleophile sulfonyl hydrazines. In addition, the stability of the product was tested by a HNMR spectrometer.

Synthesis of N-Sulfonyl Amidines and Acyl Sulfonyl Ureas from Sulfonyl Azides, Carbon Monoxide, and Amides.

A Pd-catalyzed and ligand-free carbonylation/cycloaddition/decarboxylation cascade synthesis of sulfonyl amidines from sulfonyl azides and substituted amides at low CO pressure is reported. The reaction proceeds via an initial Pd-catalyzed carbonylative generation of sulfonyl isocyanates from sulfonyl azides, followed by a [2 + 2] cycloaddition with amides and subsequent decarboxylation, which liberates the desired sulfonyl amidines, generating N2 and CO2 as the only reaction byproducts. Using this simple protocol, a diverse range of sulfonyl amidines was obtained in moderate to excellent yields. In addition, the reaction can also be directed through a more conventional amidocarbonylation pathway by employing N-monosubstituted amide nucleophiles to afford acyl sulfonyl ureas in good yields.

Synthesis of N-Sulfonylamidines by Catalyst-Free Hydroamination of Ynamides and Amines

A novel synthesis of <i>N</i>-sulfonylamidines by catalyst-free hydroamination of <i>N</i>,<i>N</i>-disulfonyl ynamides with amines was developed. Alkyl amines react with <i>N</i>,<i>N</i>-disulfonyl ynamides under mild conditions, whereas aryl amines require higher temperatures. Plausible mechanisms are proposed to explain this reaction.