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Short Paper | Regular issue | Vol 91, No. 2, 2015, pp.363-374
Published online, 7th January, 2015
DOI: 10.3987/COM-14-13109
Modification of 3,5-Dioxo-2-phenyl-2,3,4,5-tetrahydro-1,2,4-triazine-6-carbonitrile via Mitsunobu and Chan-Lam Coupling Reaction

Tomáš Ručil, Martin Grepl, and Petr Cankař*

*Department of Organic Chemistry, Palacký University, 17. listopadu 12, 77146 Olomouc, Czech Republic

Abstract

Modification of 3,5-dioxo-2-phenyl-2,3,4,5-tetrahydro-1,2,4-triazine-6-carbonitrile at position 4 is described. Alkylations were carried out under Mitsunobu reaction conditions in DCM or dioxane with alcohols containing tertiary amines, pyridine and imidazole heterocyclic systems, and Boc-protected amino groups. The scope of modifications was extended with arylations performed via Chan-Lam coupling reaction using copper(I) oxide as a catalyst in a DMF solution at room temperature. In order to further extend peripheral structural diversity the nitrile group at position 6 of several alkylated 1,2,4-triazines was transformed into the amidoxime functionality.