Pd -Catalyzed and Copper Assisted Regioselective Sequential C2 and C7 Arylation of Thiazolo[5,4-f]quinazolin-9(8H)-one with Aryl Halides

被引：23

作者：

Harari, Marine ^{[1
]}

Couly, Florence ^{[1
]}

Fruit, Corinne ^{[1
]}

Besson, Thierry ^{[1
]}

机构：

[1] Normandie Univ, UNIROUEN, INSA Rouen, CNRS,COBRA, F-76000 Rouen, France

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 13期

关键词：

H BOND FUNCTIONALIZATION; MEDIATED DIRECT ARYLATION; DIRECT CH ARYLATION; ORGANIC-SYNTHESIS; THIAZOLE DERIVATIVES; COCATALYTIC SYSTEM; DYRK1A INHIBITORS; ONE HETEROATOM; EFFICIENT; HETEROARENES;

D O I：

10.1021/acs.orglett.6b01552

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A selective functionalization of thiazolo[5,4-f]quinazolin-9(8H)-one has been developed through sequential activation of C-H bonds to furnish diarylated compounds. This strategy allows the regioselective C2 and C7 arylation by a judicious choice of coupling partners and bases, requiring no additional ligands or directing groups. Differently substituted N-8-benzylated-2,7-diaryl-thiazoloquinazolin-9(8H),ones were thereby obtained in a facile manner. A one-pot procedure was also performed. These protocols provide a synthetically useful route for late-stage functionalization of this highly valuable scaffold, required in drug discovery.

引用

页码：3282 / 3285

页数：4

共 21 条

[1] Late-Stage C-H Arylation of Thiazolo[5,4-f]quinazolin-9(8H)-one Backbone: Synthesis of an Array of Potential Kinase Inhibitors
Couly, Florence
Dubouilh-Benard, Carole
Besson, Thierry
Fruit, Corinne
SYNTHESIS-STUTTGART, 2017, 49 (20): : 4615 - 4622
[2] Late-Stage Sequential C-H Functionalization of Thiazolo[5,4-f] quinazolin-9(8H)-one: Synthesis of a Library of Potential Kinase Inhibitors
Fruit, Corinne
Harari, Marine
Couly, Florence
Besson, Thierry
20TH INTERNATIONAL ELECTRONIC CONFERENCE ON SYNTHETIC ORGANIC CHEMISTRY (ECSOC), 2016,
[3] Synthesis of Thiazolo[5,4-f]quinazolin-9(8H)-ones as Multi- Target Directed Ligands of Ser/Thr Kinases
Hedou, Damien
Godeau, Julien
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MOLECULES, 2016, 21 (05)
[4] Biological Characterization of 8-Cyclopropyl-2-(pyridin-3-yl)thiazolo[5,4-f]quinazolin-9(8H)-one, a Promising Inhibitor of DYRK1A
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[5] Development of Kinase Inhibitors via Metal-Catalyzed C-H Arylation of 8-Alkyl-thiazolo[5,4-f]-quinazolin-9-ones Designed by Fragment- Growing Studies
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Harari, Marine
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[6] Cu/Pd-Catalyzed C-2-H Arylation of Quinazolin-4(3H)-ones with (Hetero)aryl Halides
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[7] Synthesis of Bioactive 2-(Arylamino)thiazolo[5,4-f]quinazolin-9-ones via the Hugershoff Reaction or Cu- Catalyzed Intramolecular C-S Bond Formation
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[8] Sequential one-pot Rh(III)-catalyzed direct C2 and C7 alkylation of (hetero)aromatic C-H bonds of indoles
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[9] Ligand-Free Pd-Catalyzed and Copper-Assisted C-H Arylation of Quinazolin-4-ones with Aryl Iodides under Microwave Heating
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[10] Ruthenium-Catalyzed Regioselective C7-H Arylation of 2-(Het)aryl[1,2,4]triazolo[1,5-a]pyrimidines with Aryl Halides
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