Reaction of N-(tosylmethyl)ureas with NaCN: synthetic and mechanistic aspects

Anastasia Fesenko; Anatoly Shutalev

doi:10.3390/ecsoc-25-11759

Previous Article in event

Ultrasound Assisted Synthesis of 1,5-Disubstituted Tetrazoles Containing Propargyl or 2-Azidophenyl Moieties via Ugi-Azide Reaction

Next Article in event

A novel heterocyclic thiosemicarbazone: synthesis, characterization and preliminary sensing studies for ions

Next Article in session

Cyclometallated thiosemicarbazones containing fluorine atoms: a solubility improvement

Reaction of N-(tosylmethyl)ureas with NaCN: synthetic and mechanistic aspects

Anastasia Fesenko

Anatoly Shutalev

¹ N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., 119991 Moscow, Russian Federation

Academic Editor: Julio A. Seijas

Published: 14 November 2021 by MDPI in The 25th International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis

https://doi.org/10.3390/ecsoc-25-11759

Abstract:

Reaction of NaCN with N-(tosylmethyl)ureas, prepared by condensation of urea with aldehydes and p-toluenesulfinic acid, has been studied. Generally, this reaction afforded the corresponding α-ureido nitriles. Some mechanistic aspects of cyanide-anion amidoalkylation with N-(tosylmethyl)ureas were discussed based on DFT calculations.

Keywords: N-(tosylmethyl)ureas; sodium cyanide; α-amidoalkylation; α-ureido nitriles

View paper

43 Reads
0 Recommendations

Anastasia Fesenko

Anatoly Shutalev