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

被引：0

作者：

Rucil, Tomas ^{[1
]}

Grepl, Martin ^{[1
]}

Cankar, Petr ^{[1
]}

机构：

[1] Palacky Univ, Dept Organ Chem, Olomouc 77146, Czech Republic

来源：

HETEROCYCLES | 2015年 / 91卷 / 02期

关键词：

Heterocycles; Mitsunobu Reaction; Chan-Lam Coupling Reaction; 1,2,4-Triazine; N-Alkylation;

D O I：

10.3987/COM-14-13109

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：363 / 374

页数：12

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