Ytterbium-catalyzed formal [4+2] cycloaddition: Synthesis of chalcogen-quinolines 3-unsubstituted

被引：3
作者：
de Oliveira, Isadora M. [1 ]
Darbem, Mariana P. [2 ]
Esteves, C. Henrique A. [2 ]
Pimenta, Daniel C. [3 ]
Zukerman-Schpector, Julio [4 ]
Stefani, Helio A. [2 ]
Manarin, Flavia [5 ]
机构：
[1] Univ Sao Paulo, Inst Quim, Dept Quim Fundamental, Sao Paulo, SP, Brazil
[2] Univ Sao Paulo, Fac Ciencias Farmacaut, Dept Farm, Sao Paulo, Brazil
[3] Inst Butantan, Sao Paulo, SP, Brazil
[4] Univ Fed Sao Carlos, Dept Quim, Sao Carlos, SP, Brazil
[5] Univ Estadual Oeste Parana, CECE, Toledo, PR, Brazil
来源：
TETRAHEDRON LETTERS | 2018年 / 59卷 / 44期
基金：
巴西圣保罗研究基金会;
关键词：
Quinolines; Ytterbium; Poly-substituted quinolones; Selenium; Internal alkynes; POLYSUBSTITUTED QUINOLINES; SUBSTITUTED QUINOLINES; TANDEM SYNTHESIS; 5+1 ANNULATION; DERIVATIVES; SELENIUM; ALKYNES; CHEMISTRY; EFFICIENT;
D O I：
10.1016/j.tetlet.2018.09.022
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A regioselective ytterbium-catalyzed annulation reaction between ethylglyoxalate, anilines and silylalkynes bearing selenyl- and telluryl-moieties for the formation of poly-substituted quinolones is described. A series of examples formed under mild conditions are presented, including a scaled-up reaction and a study on catalyst recyclability. (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3907 / 3911
页数：5
相关论文
共 50 条
  • [21] A Comparative Investigation: Group 9 Cp*M(III)-Catalyzed Formal [4+2] Cycloaddition as an Atom-Economic Approach to Quinazolines
    Wang, Xiaoming
    Lerchen, Andreas
    Glorius, Frank
    ORGANIC LETTERS, 2016, 18 (09) : 2090 - 2093
  • [22] One-step Synthesis of 3-Unsubstituted 4-Hydroxy-2(1H)-Quinoline
    Sun Qingrong
    Wang Xingyi
    Xu Yinan
    Yang Weiqing
    Ma Menglin
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2021, 31 (03) : 435 - 441
  • [23] Gold(I)-Catalyzed Intermolecular Formal [4+2] Cycloaddition of O-Aryl Ynol Ethers and Enol Ethers: Synthesis of Chromene Derivatives
    Suarez-Rodriguez, Tatiana
    Suarez-Sobrino, angel L.
    Ballesteros, Alfredo
    CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (51) : 13079 - 13084
  • [24] Ruthenium-Catalyzed Formal Dehydrative [4+2] Cycloaddition of Enamides and Alkynes for the Synthesis of Highly Substituted Pyridines: Reaction Development and Mechanistic Study
    Wu, Jicheng
    Xu, Wenbo
    Yu, Zhi-Xiang
    Wang, Jian
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (29) : 9489 - 9496
  • [25] Formal [3+2] Cycloaddition of Ketenes and Oxaziridines Catalyzed by Chiral Lewis Bases: Enantioselective Synthesis of Oxazolin-4-ones
    Shao, Pan-Lin
    Chen, Xiang-Yu
    Ye, Song
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (45) : 8412 - 8416
  • [26] Formal [4+2] cycloaddition of cyclobutanones bearing alkyne-cobalt complex at their 3-positions
    Kawano, Mizuki
    Kiuchi, Takaaki
    Matsuo, Jun-ichi
    Ishibashi, Hiroyuki
    TETRAHEDRON LETTERS, 2012, 53 (04) : 432 - 434
  • [27] Phosphine-Catalyzed Intermolecular Annulations of Fluorinated ortho-Aminophenones with Alkynones -The Switchable [4+2] or [4+2]/[3+2] Cycloaddition
    Zhang, Yanshun
    Sun, Yaoliang
    Wei, Yin
    Shi, Min
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (09) : 2129 - 2135
  • [28] DMAP-Catalyzed [4+2] Cycloaddition of α,β-Unsaturated Carboxylic Acids with Ketones for Synthesis of α,β-Unsaturated δ-Lactones
    Jin, Jinghai
    Xu, Qinchang
    Deng, Weiping
    CHINESE JOURNAL OF CHEMISTRY, 2017, 35 (04) : 397 - 400
  • [29] Thermally induced formal [4+2] cycloaddition of 3-aminocyclobutenones with electron-deficient alkynes: facile and efficient synthesis of 4-pyridones
    Yu, Yang
    Zhang, Yan
    Xiao, Li-Yun
    Peng, Qin-Qin
    Zhao, Yu-Long
    CHEMICAL COMMUNICATIONS, 2018, 54 (59) : 8229 - 8232
  • [30] An isothiourea-catalyzed asymmetric formal [4+2] cycloaddition of in situ generated azoalkenes with C1 ammonium enolates
    Zhang, Zi-Jing
    Song, Jin
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (17): : 2578 - 2582
12345