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

Article abstract of DOI:10.3987/COM-14-13109

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.

Full text of 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 and Petr Cankař*
Department of Organic Chemistry, Palacky University, 17. listopadu 1192/12, 771 46 Olomouc, Czech Republic
E-mail:cankar@orgchem.upol.cz
Supplementary data
Table of Contents
Compound 5a.......................................................................................................................................... 3
Compound 5c.......................................................................................................................................... 3
Compound 5d ......................................................................................................................................... 5
Compound 5f .......................................................................................................................................... 6
Compound 5g.......................................................................................................................................... 7
Compound 5h ......................................................................................................................................... 8
Compound 5i .......................................................................................................................................... 9
Compound 5j ........................................................................................................................................ 10
Compound 5k........................................................................................................................................ 11
Compound 7a........................................................................................................................................ 12
Compound 7b ....................................................................................................................................... 13
Compound 7c........................................................................................................................................ 14
Compound 8h ....................................................................................................................................... 15
Compound 8j ........................................................................................................................................ 16
Compound 8k........................................................................................................................................ 17
S1

S2

Compound 5a
S3

Compound 5c
S4

Compound 5d
S5

Compound 5f
S6

Compound 5g
S7

Compound 5h
S8

Compound 5i
S9

Compound 5j
S10

Compound 5k
S11

Compound 7a
S12

Compound 7b
S13

Compound 7c
S14

Compound 8h
S15

Compound 8j
S16

Compound 8k
S17