| 63 | 0 | 35 |
| 下载次数 | 被引频次 | 阅读次数 |
以氯化碘(ICl)为催化剂,通过苯胺、乙醛酸乙酯与炔反应制备了喹啉-2-羧酸乙酯类化合物.各种炔、苯胺与乙醛酸乙酯均能顺利反应,产物收率为57%～94%.讨论了底物取代基与产物收率的关系,确证了产物的结构.
Abstract：Catalyzed by ICl, quinoline-2-carboxylic acid ethyl esters are prepared by reacting anilines, ethyl glyoxylates with alkynes. All kinds of alkynes and anilines can react with ethyl glyoxylates smoothly, and the product yields are 57%-94%. The relationship between yields and substituent groups is described. The structure of products is confirmed.
[1] KUMAR S, BAWA S, GUPTA H. Biological Activities of Quinoline Derivatives[J]. Mini Reviews in Medicinal Chemistry, 2009, 9(14):1 648-1 654.
[2] BAX B D, CHAN P F, EGGLESTON D S, etal. Type IIA Topoisomerase Inhibition by a New Class of Antibacterial Agents[J]. Nature, 2010,466(7 309):935-940.
[3]黄文静,谭超兰,张丹丹,等.喹啉羧酸及其衍生物的合成方法[J].化工时刊,2016,30(1):33-37.
[4] ANVAR S, MOHAMMADPOOR-BALTORK I, TANGESTANINEJAD S, etal. Efficient and Environmentally-benign Three-component Synthesis of Quinolines and Bis-quinolines Catalyzed by Recyclable Potassium Dodecatungstocobaltate Trihydrate Under Microwave Irradiation[J]. RSC Advances, 2012, 2(23):8 713-8 720.
[5] ELAHEH K, MALLAKMOHAMMADI M. Ultrasound Promoted Synthesis of Quinolines Using Basic Ionic Liquids in Aqueous Media as a Green Procedure[J]. Ultrasonics Sonochemistry, 2011, 18(1):447-454.
[6] CHAN S C, WEN X R. A Recyclable Palladium-catalyzed Modified Friedl覿nder Quinoline Synthesis[J]. Journal of Organometallic Chemistry, 2008, 39(2):4 182-4 186.
[7] HUANG H, JIANG H L, CHEN K X, etal. A Simple and Convenient Copper-catalyzed Tandem Synthesis of Quinoline-2-Carboxylates at Room Temperature[J]. Journal of Organic Chemistry, 2009, 74(15):5 476-5 480.
[8] YAO C, QIN B, ZHANG H, etal. One-pot Solvent-free Synthesis of Quinolines by C—H Activation/C—C Bond Formation Catalyzed by Recyclable Iron(III)Triflate[J]. RSC Advances, 2012, 2(9):3 759-3 764.
[9] DESHIDI R, DEVARI S, SHAH B A. Metal Free Access to Quinolines via C—C Bond Cleavage of Styrenes[J]. Org.Chem.Front., 2015, 2(5):515-519.
[10] LI X, MAO Z, WANG Y, etal. Molecular Iodine-catalyzed and Air-mediated Tandem Synthesis of Quinolines via Three-component Reaction of Amines, Aldehydes and Alkynes[J]. Tetrahedron, 2011, 67(21):3 858-3 862.
[11] BATCHU H, BHATTACHARYYA S, BATRA S. Iodine-mediated Intramolecular Electrophilic Aromatic Cyclization in Allylamines:A General Route to Synthesis of Quinolines, Pyrazolo[4, 3-b]pyridines and Thieno[3, 2-b]pyridines[J]. Organic Letters, 2012, 14(24):6 330-6 333.
基本信息:
DOI：10.13573/j.cnki.sjzxyxb.2018.06.005
中图分类号:TQ253.23
引用信息:
[1]张宝华,胡永青,刘宏果,等.氯化碘催化的喹啉-2-羧酸乙酯类化合物的合成[J].石家庄学院学报,2018,20(06):30-33.DOI:10.13573/j.cnki.sjzxyxb.2018.06.005.
基金信息:
河北省科技支撑项目(18271404D)
2018-11-20
2018-11-20