Synthesis of Benzoacridines and Benzophenanthridines by Regioselective Pd-Catalyzed Cross-Coupling Reactions Followed by Acid-Mediated Cycloisomerizations

被引：25

作者：

Janke, Sophie ^{[1
]}

Boldt, Sebastian ^{[1
]}

Ghazargan, Karapet ^{[2
]}

Ehlers, Peter ^{[1
,3
]}

Villinger, Alexander ^{[1
]}

Langer, Peter ^{[1
,3
]}

机构：

[1] Univ Rostock, Inst Chem, Albert Einstein Str 3a, D-18059 Rostock, Germany

[2] Yerevan State Univ, Inst Chem, 1 Alek Manukyan St, Yerevan 0025, Armenia

[3] Univ Rostock eV LIKAT, Leibniz Inst Catalysis, Albert Einstein Str 29a, D-18059 Rostock, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 2019卷 / 36期

关键词：

Cyclization; Homogeneous catalysis; Palladium; Heterocycles; Regioselectivity; FACILE SYNTHESIS; DIE TIEFTEMPERATURSPEKTREN; INTRAMOLECULAR CYCLIZATION; PHENANTHRIDINE; ACRIDINES; DERIVATIVES; BINDING; INHIBITOR; ALDEHYDES; COMPLEX;

D O I：

10.1002/ejoc.201900913

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient synthesis of various benzoacridines and benzophenanthridines from readily available dihalogenated quinolines is reported. The synthesis is based on regioselective Suzuki and Sonogashira reactions followed by Bronsted acid-mediated cycloisomerization. The developed methodology is highly modular and allows the construction of various ring systems and substitution patterns in high yields. The optical and electrochemical properties of selected derivatives were investigated.

引用

页码：6177 / 6197

页数：21

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