Salts of 5-Substituted Uracils with 1,8-Diazabicyclo[5.4.0]-undec-7-ene: Convenient Reagents for Nucleophilic Addition and Substitution Reactions

Jerzy Suwiski; Krzysztof Walczak

doi:10.1055/s-2001-10805

Synthesis 2001; 2001(2): 0225-0228
DOI: 10.1055/s-2001-10805

short paper

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Salts of 5-Substituted Uracils with 1,8-Diazabicyclo[5.4.0]-undec-7-ene: Convenient Reagents for Nucleophilic Addition and Substitution Reactions

Jerzy Suwiński^* , Krzysztof Walczak

^*Institute of Organic Chemistry and Technology, Silesian Technical University, 44-100 Gliwice, Poland; E-mail: suwinski§zeus.polsl.gliwice.pl

Abstract

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1,8-Diazabicyclo[5.4.0]-undec-7-ene (DBU) salts of 5-substituted uracils have been obtained as crystals. The salts were used as nucleophiles in the synthesis of 1-(2′-hydroxy-3′-methoxypropyl)uracils by oxirane ring opening in 1,2-epoxy-3-methoxypropane and in reversed pyrimidine nucleosides synthesis by substitution of the terminal tosylate group in methyl 6-O-tosyl-α-d-glucopyranoside.

DBU salts - nucleophilic substitution - N-alkylation - reversed nucleosides

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