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

Anatoly Shutalev; Anastasia Fesenko

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

^*,

Anastasia A. Fesenko

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

Published: 01 November 2005 by MDPI in The 9th International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis

https://doi.org/10.3390/ecsoc-9-01498

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 migration

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Anatoly Shutalev

Anastasia Fesenko