Diversity-Oriented Synthesis of Dibenzoazocines and Dibenzoazepines via a Microwave-Assisted Intramolecular A3-Coupling Reaction

被引：47

作者：

Bariwal, Jitender B. ^{[1
]}

Ermolat'ev, Denis S. ^{[1
]}

Glasnov, Toma N. ^{[3
]}

Van Hecke, Kristof ^{[2
]}

Mehta, Vaibhav P. ^{[1
]}

Van Meervelt, Luc ^{[2
]}

Kappe, C. Oliver ^{[3
]}

Van der Eycken, Erik V. ^{[1
]}

机构：

[1] Katholieke Univ Leuven, LOMAC, B-3001 Heverlee, Belgium

[2] Katholieke Univ Leuven, Dept Chem, B-3001 Heverlee, Belgium

[3] Karl Franzens Univ Graz, Inst Chem, Christian Doppler Lab Microwave Chem, A-8010 Graz, Austria

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 12期

关键词：

BIARYL COUPLING REACTION; APOGALANTHAMINE ANALOGS; ORGANIC-SYNTHESIS; DIRECT-ADDITION; ENANTIOSELECTIVE SYNTHESIS; TERMINAL ALKYNES; SUZUKI-MIYAURA; COPPER; AMINE; (-)-STEGANACIN;

D O I：

10.1021/ol1008729

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An unprecedented, diversity-oriented strategy for the generation of 6,7-dihydro-5H-dibenzo[c,e]azepines and 5,6,7,8-tetrahydrodibenzo[c,e]azocines by a microwave-assisted copper-catalyzed intramolecular A(3)-coupling reaction is presented.

引用

页码：2774 / 2777

页数：4

共 41 条

[1] Generation of a small library of highly electron-rich 2-(Hetero)aryl-substituted phenethylamines by the Suzuki-Miyaura reaction: A short synthesis of an apogalanthamine analogue [J].

Appukkuttan, P ;

Orts, AB ;

Chandran, RP ;

Goeman, JL ;

Van der Eycken, J ;

Dehaen, W ;

Van der Eycken, E .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (15) :3277-3285

[2] Suzuki-Miyaura and Stille reactions as key steps in the synthesis of diversely functionalized Amaryllidaceae alkaloid analogs bearing a 5,6,7,8-tetrahydrobenzo[c,e] azocine skeleton [J].

Appukkuttan, Prasad ;

Dehaen, Wim ;

Van der Eycken, Erik .

COMBINATORIAL CHEMISTRY & HIGH THROUGHPUT SCREENING, 2007, 10 (09) :790-801

[3] Microwave-assisted transition-metal-catalyzed synthesis of N-shifted and ring-expanded buflavine analogues [J].

Appukkuttan, Prasad ;

Dehaen, Wim ;

Van der Eycken, Erik .

CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (22) :6452-6460

[4] Microwave-assisted natural product chemistry [J].

Appukkuttan, Prasad ;

Van der Eycken, Erik .

MICROWAVE METHODS IN ORGANIC SYNTHESIS, 2006, 266 :1-47

[5] An Overview of Syntheses of Apogalanthamine Analogues and 7-Aza Derivatives of Steganacin and Steganone [J].

Appukkuttan, Prasad ;

Van der Eycken, Erik .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (35) :5867-5886

[6] Efficient Microwave-Assisted Synthesis of Secondary Alkylpropargylamines by Using A3-Coupling with Primary Aliphatic Amines [J].

Bariwal, Jitender B. ;

Ermolat'ev, Denis S. ;

Van der Eyeken, Erik V. .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (11) :3281-3284

[7] The asymmetric Suzuki coupling route to axially chiral biaryls [J].

Baudoin, O .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (20) :4223-4229

[8] Microwave-enhanced synthesis of new (-)-steganacin and (-)-steganone aza analogues [J].

Beryozkina, T ;

Appukkuttan, P ;

Mont, N ;

Van der Eycken, E .

ORGANIC LETTERS, 2006, 8 (03) :487-490

[9] Generating diverse skeletons of small molecules combinatorially [J].

Burke, MD ;

Berger, EM ;

Schreiber, SL .

SCIENCE, 2003, 302 (5645) :613-618

[10] Teaching target-oriented and diversity-oriented organic synthesis at Harvard University [J].

Burke, MD ;

Lalic, G .

CHEMISTRY & BIOLOGY, 2002, 9 (05) :535-541

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