Events The 9th International Electronic Conference on Synthetic Organic Chemistry

Event submissions

Published

This submission belongs to the session a. General Organic Synthesis of the event The 9th International Electronic Conference on Synthetic Organic Chemistry

Published date

01 Nov, 2005

Citation

Anatoly D. Shutalev, Anastasia A. Fesenko, Unexpected Tosyl Migration in Acid Catalyzed Dehydration of 4-hydroxy-4-methyl-5-tosyl-2-cyaniminohexahydropyrimidines, in Proceedings of The 9th International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2005, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-9-01498

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Unexpected Tosyl Migration in Acid Catalyzed Dehydration of 4-hydroxy-4-methyl-5-tosyl-2-cyaniminohexahydropyrimidines

Anatoly D. Shutalev ¹

Anastasia A. Fesenko ¹

1. Department of Organic Chemistry, M.V.Lomonosov State Academy of Fine Chemical Technology, 119571 Moscow, Russian Federation

Abstract

Base-catalyzed dehydration of 2-cyanimino-4-hydroxy-4-methyl-5-tosylhexahydropyrimidines gives expected 2-cyanimino-5-tosyl-1,2,3,4-tetrahydropyrimidines. However, acid-catalyzed dehydration leads to mixture of the latter compounds and the products of tosyl group migration, namely 2-cyanimino-4-tosylmethyl-1,2,3,4-tetrahydropyrimidines. Plausible explanation of the obtained data is proposed.

Keywords

N-cyanoguanidine

N-cyano-N'-(1-tosyl-1-alkyl)guanidines

tosylacetone

2-cyanimino-4-hydroxy-5-tosylhexahydropyrimidines

dehydration

2-cyanimino-5-tosyl-1,2,3,4-tetrahydropyrimidines

2-cyanimino-4-tosylmethyl-1,2,3,4-tetrahydropyrimidines

tosyl migra

Benzo[f]benzopyranones as Fluorescent Labels for Amino Acids

Preparation of Long-Chain Alkoxyethoxysulfates and Synthetic Applications