Regioselective Copper(I)-Catalyzed Direct C(3)-H (Hetero)arylation of 6-(Hetero)arylated 1,2,4-Triazolo[4,3-b]pyridazines: Ligand-Free Approach

被引：0

作者：

Hourma, Chaimae ^{[1
,2
,3
]}

Jismy, Badr ^{[1
]}

Blancou, Wafa ^{[1
]}

Driowya, Mohsine ^{[3
,4
]}

Bougrin, Khalid ^{[3
,5
]}

Guillaumet, Gerald ^{[2
,6
]}

Abarbri, Mohamed ^{[1
]}

机构：

[1] Univ Tours, Fac Sci & Technol, Lab Physico Chem Mat & Electrolytes Energy PCM2E, F-37200 Tours, France

[2] Univ Orleans, Inst Organ & Analyt Chem, CNRS, UMR 7311, BP 6759, F-45067 Orleans, France

[3] Mohammed V Univ Rabat, Nat Patrimony & Green Chem GEOPAC Res Ctr, Plant Chem & Organ & Bioorgan Synth Team, URAC23,Fac Sci,Geophys, BP 1014, Rabat 10500, Morocco

[4] Sultan Moulay Slimane Univ, Higher Sch Technol, BP 170, Khenifra 54006, Morocco

[5] Mohammed VI Polytech Univ, Chem & Biochem Sci Green Proc Engn CBS GPE, Benguerir 43150, Morocco

[6] Euromed Univ Fes UEMF, Euromed Fac Pharm, Euromed Res Ctr, Fes 30000, Morocco

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 23期

关键词：

C-H ARYLATION; CATALYZED DIRECT ARYLATION; ANXIOLYTIC ACTIVITY; 1,2,4-TRIAZOLES; 1,3,4-OXADIAZOLES; HETEROARENES;

D O I：

10.1021/acs.joc.4c00724

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first efficient Cu(I) catalyzed regioselective C3-(hetero)arylation of 6-(hetero)arylated 1,2,4-triazolo[4,3-b]pyridazines has been developed to streamline the synthesis of pharmaceutically important 3,6-diarylated 1,2,4-triazolo[4,3-b]pyridazines. This direct (hetero)arylation is compatible with a range of aryl iodides and tolerates a variety of functional groups (23 examples). A series of new 3,6-diarylated 1,2,4-triazolo[4,3-b]pyridazines were synthesized with good to excellent yields (up to 98%). The reactivity varied depending on the nature of the aryl iodide and the substituent in position 6 of the starting substrate. The procedure is experimentally simple, cost-effective, and free of additional ligands and cocatalysts.

引用

页码：16999 / 17008

页数：10