Redox condensation of o-halonitrobenzene with 1,2,3,4-tetrahydroisoquinoline: involvement of an unexpected auto-catalyzed redox cascade

被引：49

作者：

Nguyen, T. B. ^{[1
]}

Ermolenko, L. ^{[1
]}

Al-Mourabit, A. ^{[1
]}

机构：

[1] Univ Paris Saclay, Univ Paris 11, CNRS UPR 2301, Inst Chim Subst Nat, 1 Av Terrasse, F-91198 Gif Sur Yvette, France

来源：

CHEMICAL COMMUNICATIONS | 2016年 / 52卷 / 27期

关键词：

C-H ACTIVATION; BENZIMIDAZOLES; FUNCTIONALIZATION; CONSTRUCTION; RESOLUTION; AMINATION;

D O I：

10.1039/c6cc01436d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A practical synthesis of fused benzimidazoles 5 has been developed by simply heating o-halonitrobenzenes 1 with tetrahydroisoquinolines 2. In this transformation, 2 played multiple roles as a building block, base and a double hydride donor in a cascade of uncatalyzed aromatic substitution, reduction of the nitro group, oxidation of the alpha-methylene group and condensation.

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收藏

页码：4914 / 4917

页数：4

相关论文

共 28 条

[1] Aromatic homolytic substitution using solid phase synthesis [J].

Allin, SM ;

Bowman, WR ;

Karim, R ;

Rahman, SS .

TETRAHEDRON, 2006, 62 (18) :4306-4316

[2] Reduced benzimidazo[2,1-a] isoquinolines. Synthesis and cytotoxicity studies [J].

Deady, LW ;

Rodemann, T .

AUSTRALIAN JOURNAL OF CHEMISTRY, 2001, 54 (08) :529-534

[3] Redox Isomerization via Azomethine Ylide Intermediates: N-Alkyl Indoles from Indolines and Aldehydes [J].

Deb, Indubhusan ;

Das, Deepankar ;

Seidel, Daniel .

ORGANIC LETTERS, 2011, 13 (04) :812-815

[4] Retro-Claisen condensation versus pyrrole formation in reactions of amines and 1,3-diketones [J].

Deb, Indubhusan ;

Seidel, Daniel .

TETRAHEDRON LETTERS, 2010, 51 (22) :2945-2947

[5]

Endo H., 2004, [No title captured], Patent No. [EP1481965 A1, 1481965]

[6]

Fulp A. B., 2005, [No title captured], Patent No. [WO2005002503A2, 2005002503, WO 2005002503 A2]

[7] C ∼ H Bond Functionalization through Intramolecular Hydride Transfer** [J].

Haibach, Michael C. ;

Seidel, Daniel .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (20) :5010-5036

[8]

HEDLEY KA, 1995, J HETEROCYCLIC CHEM, V32, P529

[9] Design and Synthesis of Polycyclic Imidazole-Containing N- Heterocycles based on C?H Activation/Cyclization Reactions [J].

Iaroshenko, Viktor O. ;

Ostrovskyi, Dmytro ;

Miliutina, Mariia ;

Maalik, Aneela ;

Villinger, Alexander ;

Tolmachev, Andrei ;

Volochnyuk, Dmitriy M. ;

Langer, Peter .

ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (13) :2495-2503

[10] [Fe(F20TPP)Cl]-Catalyzed Amination with Arylamines and {[Fe(F20TPP)(NAr)](PhI=NAr)}+• Intermediate Assessed by High-Resolution ESI-MS and DFT Calculations [J].

Liu, Yungen ;

Chen, Guo-Qiang ;

Tse, Chun-Wai ;

Guan, Xianguo ;

Xu, Zheng-Jiang ;

Huang, Jie-Sheng ;

Che, Chi-Ming .

CHEMISTRY-AN ASIAN JOURNAL, 2015, 10 (01) :100-105