Facile synthesis of functionalized 1H-pyrrolo[2,3-b]quinolines via Ugi four-component reaction followed by Cu-catalyzed aryl-amide, C-N bond coupling

被引：23
|
作者：
Asthana, Mrityunjaya [1 ]
Kumar, Ritush [1 ]
Gupta, Tanu [1 ]
Singh, Radhey M. [1 ]
机构：
[1] Banaras Hindu Univ, Dept Chem, Ctr Adv Study, Varanasi 221005, Uttar Pradesh, India
来源：
TETRAHEDRON LETTERS | 2015年 / 56卷 / 07期
关键词：
1H-Pyrrolo[2,3-b]quinolines; One-pot; Ugi reaction; Copper-catalyzed; 1,4]Oxazine; ONE-POT SYNTHESIS; MULTICOMPONENT REACTIONS; EFFICIENT SYNTHESIS; 3-COMPONENT REACTION; BICYCLIC LACTAMS; SEQUENTIAL UGI; DIVERSE ROUTE; COPPER; DERIVATIVES; PYRROLOQUINOLINES;
D O I：
10.1016/j.tetlet.2014.12.140
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A simple one-pot two-step reaction comprising an Ugi four-component reaction (Ugi-4CR) and coppercatalyzed intramolecular amide-aryl cyclization of heteroaryl chloride with amide has been developed for the synthesis of functionalized 1H-pyrrolo[2,3-b]quinolines in moderate to good yields. The synthesized pyrrolo-fused quinoline was further examined for Pd-catalyzed intramolecular cyclization to afford [1,4]oxazine-fused pyrrolo quinoline 11 and to nucleophilic substitution reactions with allyl bromide and methyl iodide to afford the corresponding allyl and methyl ethers, 12 and 13, respectively. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码：907 / 912
页数：6
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