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

Read Full Text PDF DownLoad Join now for total 90,000,000 free articles

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

Products guided by the article

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

Cas No:66707-12-8

R&D Labs maybe for 66707-12-8

Zibo Fuxi'er Chemical Co.,Ltd （Shanxian Fuxi'er Chemical Co.,Ltd）

Contact:+86-533-2091422

Address:Eastern 4 on the 3th Road ,Liangxiang Industrial Park, Zibo city ,Shandong,China
Jining tiansheng chemical co.,ltd.

Contact:+86-537-5158722

Address:ROOM 1011, BLOCK B, CUIDU INTERNATIOAL BUSINESS CENTER, JINING CITY, CHINA
Landz International Company Ltd.

Contact:0086-21-58891610

Address:985 Dongfang Road, Pudong, Shanghai 200122 China
Huaian Double Win Chemicals Co.,Ltd.

Contact:+86-13511538872

Address:Blk 43,Greenland Century Town,Huaian District, Huaian City,Jiangsu Province,China
MINS GROUP CO.,LIMITED

Contact:18669908765

Address:Zibo City, Shandong Province, P.R.China

Relevant to this article

ANALYSIS BY THE REDUCTIVE-CLEAVAGE METHOD OF LINKAGE POSITIONS IN A POLYSACCHARIDE CONTAINING 4-LINKED D-GLUCOPYRANOSYLURONIC RESIDUES

Doi:10.1016/0008-6215(88)80159-9
(1988)
Synthesis and crystal structures of copper(I) iodide complexes chelating with bis(ethylamidophosphine)

Doi:10.1016/j.inoche.2003.09.003
(2003)
Stereoselective synthesis of functionalised cycloalkene α-quaternary α-amino acid derivatives

Doi:10.1016/j.tetasy.2003.10.013
(2004)
Organolanthanide-Catalyzed Intramolecular Hydroamination/Cyclization/Bicyclization of Sterically Encumbered Substrates. Scope, Selectivity, and Catalyst Thermal Stability for Amine-Tethered Unactivated 1,2-Disubstituted Alkenes

Doi:10.1021/jo035417c
(2004)
Synthesis and Resolution of 1-(2-Diphenylphosphino-1-naphthyl)isoquinoline; a P-N Chelating Ligand for Asymmetric Catalysis

Doi:10.1016/S0957-4166(00)80183-4
(1993)
Piperazine clubbed with 2-azetidinone derivatives suppresses proliferation, migration and induces apoptosis in human cervical cancer HeLa cells through oxidative stress mediated intrinsic mitochondrial pathway

Doi:10.1007/s10495-018-1439-x
(2018)

Article Doi