Copper-Catalyzed N-Arylation of 2-Imidazolines with Aryl Iodides

被引：22

作者：

Davis, Owen A. ^{[1
]}

Hughes, Matthew ^{[1
]}

Bull, James A. ^{[1
]}

机构：

[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 07期

基金：

英国工程与自然科学研究理事会;

关键词：

ONE-POT SYNTHESIS; COUPLING REACTIONS; PRIMARY ARYLAMINES; IMIDAZOLINES; 1,2-DIARYL-2-IMIDAZOLINES; CYCLIZATION; COMPLEXES; CHEMISTRY; DISCOVERY; CHLORIDES;

D O I：

10.1021/jo400120r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first copper-catalyzed N-arylation of 2-imidazolines is described. The reaction affords compounds with desirable lead-like characteristics in high yield with practical simplicity under inexpensive, "ligand-free" conditions. The cross coupling was successful with electron-rich and electron-poor aromatic iodides. Substrates bearing halides, esters, nitriles, and free hydroxyls are well tolerated, providing reactive handles for further functionalization, as are pyridines. In addition, the regioselective N-arylation of a 4-substituted imidazoline is reported.

引用

页码：3470 / 3475

页数：6

共 48 条

[1] METAL-IONS AND COMPLEXES IN ORGANIC REACTIONS .15. COPPER-CATALYZED SUBSTITUTIONS OF ARYL HALIDES BY PHTHALIMIDE ION [J].

BACON, RGR ;

KARIM, A .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (03) :272-278

[2] A Facile and Efficient Synthesis of 2-Imidazolines from Aldehydes Using Hydrogen Peroxide and Substoichiometric Sodium Iodide [J].

Bai, Guo-yi ;

Xu, Kai ;

Chen, Guo-feng ;

Yang, Yong-hui ;

Li, Tian-yu .

SYNTHESIS-STUTTGART, 2011, (10) :1599-1603

[3] Bisindole alkaloids of the topsentin and hamacanthin classes from a marine sponge Spongosorites sp. [J].

Bao, Baoquan ;

Sun, Qishi ;

Yao, Xinsheng ;

Hong, Jongki ;

Lee, Chong-O. ;

Cho, Hee Young ;

Jung, Jee H. .

JOURNAL OF NATURAL PRODUCTS, 2007, 70 (01) :2-8

[4] Copper in cross-coupling reactions - The post-Ullmann chemistry [J].

Beletskaya, IP ;

Cheprakov, AV .

COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2337-2364

[5] 1,2-DIAMINE AND 1,3-DIAMINE EXCHANGE BETWEEN SUBSTITUTED 4,5-DIHYDROIMIDAZOLES AND 1,4,5,6-TETRAHYDROPYRIMIDINES - ROUTES TO BENZIMIDAZOLES, DIHYDROIMIDAZOLES, AND TETRAHYDROPYRIMIDINES [J].

BUTLER, RN ;

FITZGERALD, KJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (01) :155-157

[6]

Clayton J., 2006, PCT Int. Appl., Patent No. [WO 2006/020879, 2006020879]

[7] A rule of three for fragment-based lead discovery? [J].

Congreve, M ;

Carr, R ;

Murray, C ;

Jhoti, H .

DRUG DISCOVERY TODAY, 2003, 8 (19) :876-877

[8] Ligand-Free Copper-Catalyzed Arylation of Amidines [J].

Cortes-Salva, Michelle ;

Garvin, Corey ;

Antilla, Jon C. .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (05) :1456-1459

[9] Highly efficient and mild copper-catalyzed N- and C-arylations with aryl bromides and iodides [J].

Cristau, HJ ;

Cellier, PP ;

Spindler, JF ;

Taillefer, M .

CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (22) :5607-5622

[10] Catalytic, enantioselective synthesis of stilbene cis-diamines: A concise preparation of (-)-Nutlin-3, a potent p53/MDM2 inhibitor [J].

Davis, Tyler A. ;

Johnston, Jeffrey N. .

CHEMICAL SCIENCE, 2011, 2 (06) :1076-1079

← 1 2 3 4 5 →