Temperature dependent selective synthesis of linear 2-bromo and 2-alkoxyfuro[2,3-b]quinolines: reaction of 3-(2,2-dibromovinyl-)quinolin-2(1H)-ones with alcoholic KOH

被引：22
|
作者：
Nandini, Durgesh [1 ,2 ]
Asthana, Mrityunjaya [1 ]
Mishra, Kalpana [1 ]
Singh, R. P. [2 ]
Singh, Radhey M. [1 ]
机构：
[1] Banaras Hindu Univ, Dept Chem, Ctr Adv Studies, Varanasi 221005, Uttar Pradesh, India
[2] Ctr Fire Explos & Environm Safety, Delhi 54, India
来源：
TETRAHEDRON LETTERS | 2014年 / 55卷 / 45期
关键词：
2-Chloro-3-(2,2-dibromovinyl)quinoline; 3-(2,2-Dibromovinyl)quinolin-2(1H)-ones; Alcoholic KOH; 2-Bromofuro[2,3-b]quinolines; 2-Alkoxyfuro[2,3-b]quinolines; Temperature dependent; ONE-POT SYNTHESIS; FACILE SYNTHESIS; AROMATIC HYDROXYLATION; QUINOLINE ALKALOIDS; FUROQUINOLINE; DICTAMNINE; BIOSYNTHESIS; CYCLIZATION; 2-CHLORO-3-FORMYLQUINOLINES; QUINAZOLINE;
D O I：
10.1016/j.tetlet.2014.09.082
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Base promoted and temperature dependent reactions of 3-(2,2-dibromovinyl)quinolin-2(1H)-ones have been described. At 50 degrees C, the cyclization reactions afforded 2-bromofuro[2,3-b]quinolines in good yields. However, at elevated temperature (80 degrees C) the domino reaction proceeded affording 2-alkoxyfuro [2,3-b]quinolines via cyclization and nucleophilic substitution reactions. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6257 / 6262
页数：6
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