Synthesis of δ-Carbolines via a Pd-Catalyzed Sequential Reaction from 2-Iodoanilines and N-Tosyl-enynamines

被引：48

作者：

Cao, Jian ^{[1
]}

Xu, Yongping ^{[1
]}

Kong, Long ^{[1
]}

Cui, Yuming ^{[1
]}

Hu, Ziqiang ^{[1
]}

Wang, Guanhai ^{[1
]}

Deng, Yuan ^{[1
]}

Lai, Guoqiao ^{[1
]}

机构：

[1] Hangzhou Normal Univ, Key Lab Organosilicon Chem & Mat Technol, Minist Educ, Hangzhou 310012, Zhejiang, Peoples R China

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 01期

关键词：

SOLID-PHASE SYNTHESIS; SUBSTITUTED INDOLINES; EFFICIENT SYNTHESIS; INTERNAL ALKYNES; YNAMIDES; DERIVATIVES; CYCLIZATION; INDOLES; ANALOGS; ISOMERIZATION;

D O I：

10.1021/ol2027762

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile Pd-catalyzed sequential reaction has been developed for the synthesis of delta-carbolines from 2-Iodoanilines and N-tosyl-enynamines. This protocol involves Larock heteroannulation/elimination/electrocyclization/oxidative aromatization cascade sequences and allows access to multisubstituted delta-carbolines in moderate to good yields.

引用

页码：38 / 41

页数：4

共 46 条

[1] First total synthesis of antiostatin A1, a potent carbazole-based naturally occurring antioxidant [J].

Alayrac, Carole ;

Schollmeyer, Dieter ;

Witulski, Bernhard .

CHEMICAL COMMUNICATIONS, 2009, (12) :1464-1466

[2] Electrophile-Driven Regioselective Synthesis of Functionalized Quinolines [J].

Ali, Shaukat ;

Zhu, Hai-Tao ;

Xia, Xiao-Feng ;

Ji, Ke-Gong ;

Yang, Yan-Fang ;

Song, Xian-Rong ;

Liang, Yong-Min .

ORGANIC LETTERS, 2011, 13 (10) :2598-2601

[3] New synthesis of benzo-δ-carbolines, cryptolepines, and their salts:: In vitro cytotoxic, antiplasmodial, and antitrypanosomal activities of δ-caribolines, benzo-δ-carbolines, and cryptolepines [J].

Arzel, E ;

Rocca, P ;

Grellier, P ;

Labaeïd, M ;

Frappier, F ;

Guéritte, F ;

Gaspard, C ;

Marsais, F ;

Godard, A ;

Quéguiner, G .

JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (06) :949-960

[4] A novel one-pot pyrrole synthesis via a coupling-isomerization-Stetter-Paal-knorr sequence [J].

Braun, RU ;

Zeitler, K ;

Muller, TJJ .

ORGANIC LETTERS, 2001, 3 (21) :3297-3300

[5] Solid-phase synthesis of heterocyclic nucleoside analogues: Substituted uracils tethered to isoxazoles, isoxazolines, and triazoles from a selenopolystyrene resin [J].

Cao, Jian ;

Huang, Xian .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2008, 10 (04) :526-533

[6] Facile Synthesis of Selenium/Sulfur-Substituted 3-Oxa-bicyclo[4.2.0]octa-1(8),5-diene and Tetrahydro-1H-isochromene via Sequential Three-Component Conjugate Addition/Condensation/Elimination/[2+2] or [4+2] Cyclization Reactions [J].

Cao, Jian ;

Huang, Xian ;

Wu, Luling .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (05) :1440-1443

[7] Synthesis of 2-Azaanthracenes via a Sequential Sonogashira Coupling/Alkynyl Imine-Allenyl Imine Isomerization/Aza-Diels-Alder/Elimination-Aromatization Reaction [J].

Cao, Jian ;

Yang, Xiongfa ;

Hua, Xilin ;

Deng, Yuan ;

Lai, Guoqiao .

ORGANIC LETTERS, 2011, 13 (03) :478-481

[8] Facile Synthesis of Tetrahydro-1H-isoindolones via a Sequential Three-Component Copper-Catalyzed Coupling/Propargyl-Allenyl Isomerization/[4+2] Cyclization Reaction [J].

Cao, Jian ;

Huang, Xian .

ORGANIC LETTERS, 2010, 12 (21) :5048-5051

[9] Solid-Phase Synthesis of Bis-Heterocyclic Compounds with Skeletal Diversity from Resin-Bound 3-Propargylamino-2-seleno-ester [J].

Cao, Jian ;

Huang, Xian .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2010, 12 (01) :1-4

[10] Copper-Mediated Coupling of 1,1-Dibromo-1-alkenes with Nitrogen Nucleophiles: A General Method for the Synthesis of Ynamides [J].

Coste, Alexis ;

Karthikeyan, Ganesan ;

Couty, Francois ;

Evano, Gwilherm .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (24) :4381-4385

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