Synthesis of pyrrolo-[2,1-j]quinolone framework via intramolecular electrophilic ipso-cyclization

被引：21

作者：

Low-Beinart, Lila ^{[1
]}

Sun, Xiaohan ^{[1
]}

Sidman, Eli ^{[1
]}

Kesharwani, Tanay ^{[1
]}

机构：

[1] Bard Coll, Chem Program, Annandale On Hudson, NY 12504 USA

来源：

TETRAHEDRON LETTERS | 2013年 / 54卷 / 11期

基金：

美国国家科学基金会;

关键词：

Electrophilic cyclization; Iodocyclization; Intramolecular ipso-cyclization; 1H-Pyrrolo-[2,1-j]quinolone; ASCIDIAN CLAVELINA-CYLINDRICA; DIELS-ALDER REACTION; SELECTIVE SYNTHESIS; TERMINAL ACETYLENES; LEPADIFORMIS MULLER; ALKALOIDS; (-)-LEPADIFORMINE; HALOCYCLIZATION; LIBRARY; ALKYNES;

D O I：

10.1016/j.tetlet.2012.12.014

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The challenging pyrrolo-12,1-j]quinolone core structure has been synthesized from N-(alkynoyl)-6-methoxytetrahydroquinoline in good yields using electrophilic cyclization as the key step. These reactions require simple starting materials and mild reaction conditions. In addition, we have demonstrated that the iodine moiety, which could be easily introduced in the final step, is very useful for further functionalization by employing various palladium-catalyzed cross-coupling reactions. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：1344 / 1347

页数：4

共 41 条

[1] Synthesis of Pyrrolo-[2,1-j]quinolone framework via intramolecular ipso-Iodocyclization
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ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244
[2] Na2S2O8-Promoted Radical Cyclization for the Synthesis of Azaspiro[4.5]deca-3,6,9-triene-2,8-dione and Pyrrolo[2,1-j]quinolone Derivatives
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[3] Synthesis of spirodienones by electrophiuc intramolecular IPSO-cyclization of N-(2-alkynyl)-N-(4-methoxyphenyl)amides.
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[5] Controllable Diastereodivergent Synthesis of Pyrrolo[2,1-a]isoquinolines via Catalytic Intramolecular Acylsulfenylation of Activated Alkenes
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[6] ORGN 235-Synthesis of indolo- and pyrrolo[2,1-a]isoquinolines and [1,2-a]quinolines by the electrophilic cyclization of alkynes
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[7] An efficient synthesis of pyrrolo[2,1-c][1,4]benzodiazepine antibiotics via reductive cyclization
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[8] Stereoselective Synthesis of Pyrrolo/Pyrido[2,1-a]isoindoles via Alkyne Iminium Ion Cyclization of Vinylogous Carbamates
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[9] Metal-free synthesis of benzimidazo[2,1-a]ellipticines via tandem inter and intramolecular cyclization
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[10] Synthesis of pyrrolo[2,1-c][1,4]benzodiazepine antibiotics via azido reductive cyclization with HMDST
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