Palladium-Catalyzed C-H Alkoxycarbonylation of Caffeines: Synthesis of 8-Ester-substituted Caffeines

被引：1
|
作者：
Su, Lu [1 ]
Xiao, Hanbing [1 ]
Yuan, Yumeng [1 ]
Zhang, Xiaofeng [1 ]
Lin, Shen [1 ]
Huang, Qiufeng [1 ,2 ]
机构：
[1] Fujian Normal Univ, Coll Chem & Chem Engn, Fuzhou 350007, Peoples R China
[2] Fujian Key Lab Polymer Mat, Fuzhou 350007, Peoples R China
来源：
CHINESE JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 37卷 / 03期
基金：
中国国家自然科学基金;
关键词：
palladium; C-H bond acitivation; carbonylation; caffeine; carbon monoxide; OXIDATIVE CARBONYLATION; ARYL BROMIDES; BONDS; PROBES; ACTIVATION; ANALOGS; HYDROCARBONS; HETEROARENES; HETEROCYCLES; DISCOVERY;
D O I：
10.6023/cjoc201610028
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Carbonyl-substituted caffeine derivatives have attracted much attention due to their potent pharmaceutical activity and interesting fluorescent properties. An efficient synthesis of 8-ester-substituted caffeines through palladium-catalyzed C-H alkoxycarbonylation was developed. The reaction was carried out in the presence of PdCl2(PPh3)(2) and Cu(OAc)(2) under 101 kPa CO atmosphere in 1,4-dioxane, providing diversified 8-ester-substituted caffeines in reasonable to good yields. The approach was characterized by using atmospheric pressure of carbon monoxide and broad functional group tolerance.
引用
收藏
页码：630 / 635
页数：6
相关论文
共 48 条
  • [1] Novel 1,3-Dipropyl-8-(3-benzimidazol-2-yl-methoxy-1-methylpyrazol-5-yl)xanthines as Potent and Selective A2B Adenosine Receptor Antagonists
    Baraldi, Pier Giovanni
    Baraldi, Stefania
    Saponaro, Giulia
    Preti, Delia
    Romagnoli, Romeo
    Piccagli, Laura
    Cavalli, Andrea
    Recanatini, Maurizio
    Moorman, Allan R.
    Zaid, Abdel Naser
    Varani, Katia
    Borea, Pier Andrea
    Tabrizi, Mojgan Aghazadeh
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 (02) : 797 - 811
  • [2] Palladium-Catalyzed Carbonylation-A Reaction Come of Age
    Barnard, Christopher F. J.
    [J]. ORGANOMETALLICS, 2008, 27 (21) : 5402 - 5422
  • [3] Carboxylation of C-H Bonds Using N-Heterocyclic Carbene Gold(I) Complexes
    Boogaerts, Ine I. F.
    Nolan, Steven P.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (26) : 8858 - +
  • [4] Palladium-Catalyzed Carbonylation Reactions of Aryl Halides and Related Compounds
    Brennfuehrer, Anne
    Neumann, Helfried
    Beller, Matthias
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (23) : 4114 - 4133
  • [5] Palladium-Catalyzed Oxidative Carbonylation of Aromatic C-H Bonds of N-Alkylanilines with CO and Alcohols for the Synthesis of o-Aminobenzoates
    Chen, Ming
    Ren, Zhi-Hui
    Wang, Yao-Yu
    Guan, Zheng-Hui
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (02): : 1258 - 1263
  • [6] Palladium-Catalyzed Oxidative Carbonylation of the Alkenyl C-H Bonds of Enamides: Synthesis of 1,3-Oxazin-6-ones
    Chen, Ming
    Ren, Zhi-Hui
    Wang, Yao-Yu
    Guan, Zheng-Hui
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (52) : 14196 - 14199
  • [7] Transition metal-catalyzed C-H bond functionalizations by the use of diverse directing groups
    Chen, Zhengkai
    Wang, Binjie
    Zhang, Jitan
    Yu, Wenlong
    Liu, Zhanxiang
    Zhang, Yuhong
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (09): : 1107 - 1295
  • [8] ANALOGS OF CAFFEINE AND THEOPHYLLINE - EFFECT OF STRUCTURAL ALTERATIONS ON AFFINITY AT ADENOSINE RECEPTORS
    DALY, JW
    PADGETT, WL
    SHAMIM, MT
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (07) : 1305 - 1308
  • [9] C-H carboxylation of heteroarenes with ambient CO2
    Fenner, Sabine
    Ackermann, Lutz
    [J]. GREEN CHEMISTRY, 2016, 18 (13) : 3804 - 3807
  • [10] Recent developments in palladium catalysed carbonylation reactions
    Gadge, Sandip T.
    Bhanage, Bhalchandra M.
    [J]. RSC ADVANCES, 2014, 4 (20) : 10367 - 10389
12345