Events The 25th International Electronic Conference on Synthetic Organic Chemistry

Event submissions

Published

This submission belongs to the session S1. General Organic Synthesis of the event The 25th International Electronic Conference on Synthetic Organic Chemistry

Published date

14 Nov, 2021

Academic Editor

Julio A. Seijas

Citation

Anatoly Shutalev, Anastasia Fesenko, Reaction of N-(tosylmethyl)ureas with NaCN: synthetic and mechanistic aspects, in Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry, 15 November–30 November 2021, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-25-11759

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

Anastasia Fesenko ¹

Anatoly Shutalev ²

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

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

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

Manuscript

sciforum_051670.pdf

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