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

DOI: 10.3987/COM-14-13109

Source and publish data:

Heterocycles p. 363 - 374 (2015)

Update date:2022-08-04

Topics:

Authors:

Ruil, Tom

Grepl, Martin

Canka, Petr

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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

Compound 5a

Compound 5c

Compound 5d

Compound 5f

Compound 5g

Compound 5h

Compound 5i

Compound 5j

S10

Compound 5k

S11

Compound 7a

S12

Compound 7b

S13

Compound 7c

S14

Compound 8h

S15

Compound 8j

S16

Compound 8k

S17

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Product name:3,5-dioxo-2,4-diphenyl-2,3,4,5-tetrahydro-1,2,4-triazine-6-carbonitrile

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