Efficient synthesis of 2,3,4-trisubstituted furans from the reaction of activated acetylenes with ethyl bromopyruvate in the presence of enaminones

被引:0
|
作者
Issa Yavari
Zinatossadat Hossaini
Maryam Sabbaghan
机构
[1] Tarbiat Modares University,Chemistry Department
关键词
Ethyl bromopyruvate; Activated acetylenes; Trisubstituted furans; Enaminone.;
D O I
暂无
中图分类号
学科分类号
摘要
The reaction of dialkyl acetylenedicarboxylates or diaroylacetylenes with ethyl bromopyruvate in the presence of enaminones led to 2-ethyl 3,4-dialkyl 4-bromo-4,5-dihydro-2,3,4-furantricarboxylates or ethyl 3,4-diaroyl-4-bromo-4,5-dihydro-2-furancarboxylate in excellent yields. These compounds are quantitatively converted to the corresponding 2,3,4-trisubstituted furans by 4-dimethylaminopyridine.
引用
收藏
页码:945 / 948
页数:3
相关论文
共 50 条
  • [21] Base-promoted C-C bond cleavage for the synthesis of 2,3,4-trisubstituted pyrroles from N-propargyl -enaminones
    Ge, Bailu
    Lv, Weiwei
    Yu, Jia
    Xiao, Shangyun
    Cheng, Guolin
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (21): : 3103 - 3107
  • [22] SYNTHESIS OF AN UNUSUAL 2,3,4-TRISUBSTITUTED INDOLE DERIVATIVE FOUND IN THE ANTIBIOTIC NOSIHEPTIDE
    KOERBERPLE, K
    MASSIOT, G
    SYNLETT, 1994, (09) : 759 - 760
  • [23] Synthesis of 2,3,4-trisubstituted thiochromanes using an organocatalytic enantioselective tandem Michael-Henry reaction
    Dodda, Rajasekhar
    Goldman, Joshua J.
    Mandal, Tanmay
    Zhao, Cong-Gui
    Broker, Grant A.
    Tiekink, Edward R. T.
    ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (04) : 537 - 541
  • [24] Palladium-Catalyzed Synthesis of 2,3,4-Trisubstituted Furans via Cascade Reactions of Aryloxy-enynes with Aryl Halides
    Li, Ende
    Cheng, Xingcan
    Wang, Chengyu
    Shao, Yushang
    Li, Yanzhong
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (17): : 7744 - 7748
  • [25] Enantioselective synthesis of a 2,3,4-trisubstituted pyrrolidine from 1-hydroxymethyl-4-phenylsulfonylbutadiene
    Díez, D
    Beneitez, MT
    Marcos, IS
    Garrido, NM
    Basabe, P
    Urones, JG
    SYNLETT, 2001, (05) : 655 - 657
  • [26] Nickel-Catalyzed Enantioselective Synthesis of 2,3,4-Trisubstituted 3-Pyrrolines
    Tambe, Shrikant D.
    Ka, Cheol Hyeon
    Hwang, Ho Seong
    Bae, Jaehan
    Iqbal, Naeem
    Cho, Eun Jin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (29)
  • [27] Synthesis of 2,3-di- and 2,3,4-trisubstituted furans from 1,2-dioxines generated by an enyne-RCM/Diels-Alder reaction sequence
    Yang, YK
    Choi, JH
    Tae, J
    JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (17): : 6995 - 6998
  • [28] Ring-opening cyclization of alkylidenecyclopropyl ketones with amines. An efficient synthesis of 2,3,4-trisubstituted pyrroles
    Lu, LH
    Chen, GF
    Ma, SM
    ORGANIC LETTERS, 2006, 8 (05) : 835 - 838
  • [29] A modular approach to the synthesis of 2,3,4-trisubstituted tetrahydrofurans (vol 3, pg 3119, 2006)
    Nasveschuk, Christopher G.
    Jui, Nathan T.
    Rovis, Tomislav
    CHEMICAL COMMUNICATIONS, 2006, (39) : 4145 - 4145
  • [30] The utilization of Rink amide resin in the solid phase synthesis of 2,3,4-trisubstituted pyrroles
    Sellitto, Eric
    McCranor, Bryan
    Burnham, Bruce S.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 231