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

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[38] Synthesis of 3,4-dihydrobenzo[g]isoquinoline-1(2H)-ones and 3,4-dihydroisoquinoline-1 (2H) ones skeleton via intramolecular electrophilic cyclization
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[39] Synthesis of pyrrolo[2,1-f][1,2,4]triazin-4(3H)-ones: Rearrangement of pyrrolo[1,2-d][1,3,4]oxadiazines and regioselective intramolecular cyclization of 1,2-biscarbamoyl-substituted 1H-pyrroles
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