One-pot synthesis of 2-methylfurans from 3-(trimethylsilyl)propargyl acetates promoted by trimethylsilyl trifluoromethanesulfonate

被引：5
|
作者：
Sklar, Danielle E. [1 ]
Helbling, Alex, V [1 ]
Liu, Yiqi [1 ]
Downey, C. Wade [1 ]
机构：
[1] Univ Richmond, Gottwald Ctr Sci, 138 UR Dr, Richmond, VA 23173 USA
来源：
TETRAHEDRON LETTERS | 2021年 / 87卷
基金：
美国国家科学基金会;
关键词：
Furan synthesis; Silyl triflate; One-pot reactions; Cyclizations; RING-SYSTEMS FURANS; NUCLEOPHILIC-SUBSTITUTION; PROPARGYLIC ACETATES; INHIBITION; ESTERS; ENTRY;
D O I：
10.1016/j.tetlet.2021.153424
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
In the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf) and triethylamine, 3-(trimethylsilyl)propargyl carboxylates undergo a one-pot alkylation-cyclization-desilylation reaction with ketones to produce 2-methylfurans. Alkylation at 0 degrees C in methylene chloride, followed by acid-catalyzed cyclization at room temperature, provides the furans in 52-86% yield. Cyclization and desilylation appear to be promoted by triflic acid generated in situ from the exposure of the reaction mixture to water upon completion of the initial substitution reaction. (c) 2021 Elsevier Ltd. All rights reserved.
引用
收藏
页数：4
相关论文
共 50 条
  • [41] One-Pot Sulfoxide Synthesis Exploiting a Sulfinyl-Dication Equivalent Generated from a DABSO/Trimethylsilyl Chloride Sequence
    Lenstra, Danny C.
    Vedovato, Vincent
    Flegeau, Emmanuel Ferrer
    Maydom, Jonathan
    Willis, Michael C.
    ORGANIC LETTERS, 2016, 18 (09) : 2086 - 2089
  • [42] One-pot synthesis of symmetrical bisarylethynes using bis(trimethylsilyl) acetylene and a modification of the Sonogashira coupling reaction
    Brooks, Allen F.
    Dagher, Batoul S.
    Guina, Jeffrey P.
    Labut, Anne E.
    Mio, Matthew J.
    Ball, Nicholas D.
    Marlier, Elodie E.
    Brisbois, Ronald G.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 231
  • [43] One-pot synthesis of 2-arylbenzoxazoles promoted by heteropolyacids
    Heravi, Majid M.
    Sadjadi, Samaheh
    Oskooie, Hossein A.
    Shoar, Rahim Hekmat
    Bamoharram, Fatemeh F.
    JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2008, 55 (04) : 890 - 895
  • [44] NOVEL ONE-POT SYNTHESIS OF 1-IODO-1-TRIMETHYLSILYL 1,3-DIENES
    SHEN, YC
    WANG, TL
    XIA, W
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (03): : 389 - 391
  • [45] ONE-POT SYNTHESIS OF 1-ARYLINDOLE-3-CARBOXYLATES FROM 2-(2-ISOCYANOPHENYL)ACETATES
    Fukamachi, Shuhei
    Konishi, Hisatoshi
    Kobayashi, Kazuhiro
    HETEROCYCLES, 2009, 78 (01) : 161 - 168
  • [46] A One-Pot Synthesis of Pyranocoumarins Through Microwave-Promoted Propargyl Claisen Rearrangement/Wittig Olefination
    Schmidt, Bernd
    Schultze, Christiane
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (02) : 223 - 227
  • [47] One-pot synthesis of glycidyl propargyl ether from acetylene, formaldehyde, and epichlorohydrin
    Stankevich, VK
    Klimenko, GR
    Kukharev, BF
    Trofimov, BA
    RUSSIAN JOURNAL OF APPLIED CHEMISTRY, 2000, 73 (01) : 174 - 175
  • [48] One-pot diastereoselective synthesis of α-aminonitriles from aldehydes, chiral amines, and trimethylsilyl cyanide under solvent-free conditions
    Kazemeini, A
    Azizi, N
    Saidi, MR
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 42 (01) : 48 - 51
  • [49] One-pot diastereoselective synthesis of α-aminonitriles from aldehydes, chiral amines, and trimethylsilyl cyanide under solvent-free conditions
    A. Kazemeini
    N. Azizi
    M. R. Saidi
    Russian Journal of Organic Chemistry, 2006, 42 : 48 - 51
  • [50] Single-Step Synthesis of Iodinated Oxazoles from N-Propargyl Amides Mediated by I2/lodosylbenzene/Trimethylsilyl Trifluoromethanesulfonate Systems
    Suzuki, Sho
    Saito, Akio
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (22): : 11859 - 11864
12345