Regioselective Metal-Free One-Pot Synthesis of Functionalized 2-Aminothiophene Derivatives

被引：56
|
作者：
Luo, Xiaoyan [1 ]
Ge, Li-Shi
An, Xing-Lan
Jin, Jing-Hai
Wang, Yu
Sun, Pei-Pei
Deng, Wei-Ping
机构：
[1] E China Univ Sci & Technol, Shanghai Key Lab Funct Mat Chem, Shanghai 200237, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 09期
关键词：
ENE-YNE-KETONES; SUBSTITUTED THIOPHENES; MOLECULAR DESIGN; CARBENE-TRANSFER; S-ALKENYLATION; EFFICIENT; PYRROLES; CYCLIZATION; FACILE; FURANS;
D O I：
10.1021/acs.joc.5b00488
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A facile metal-free synthesis of 2-aminothiophene derivatives by the reaction of 2-ynals with thioamides in alcohols has been developed. This transformation allows the assembly of 2-aminothienyl ether derivative via a well-designed aldol condensation/regioselective intramolecular cyclization/conjugate addition cascade reaction and provides a straightforward synthetic protocol for constructing 2-,3,5-trisubstituted 2-aminothiophenes.
引用
收藏
页码：4611 / 4617
页数：7
相关论文
共 50 条
  • [1] Metal-free One-pot Synthesis of Functionalized Carbazoles
    Tao, Sheng
    Wang, Rong-Jie
    Liu, Ning
    Dai, Bin
    CHEMISTRYSELECT, 2017, 2 (07): : 2282 - 2287
  • [2] A concise synthesis of 2-(2-aminothiophene)-benzimidazoles by one-pot multicomponent reaction
    Chen, Li-Hsun
    Chuang, Ying-Sheng
    Narhe, Bharat D.
    Sun, Chung-Ming
    RSC ADVANCES, 2013, 3 (33) : 13934 - 13943
  • [3] Metal-Free One-Pot Domino Synthesis of Oxazolidinone Derivatives
    Mandal, S.
    Kumar, A. Vijay
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 11 (03)
  • [4] One-pot regioselective synthesis of highly functionalized chromone derivatives
    Bam, Radha
    Chalifoux, Wesley
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253
  • [5] Metal-Free One-Pot Synthesis of Benzofurans
    Ghosh, Raju
    Stridfeldt, Elin
    Olofsson, Berit
    CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (29) : 8888 - 8892
  • [6] A FACILE SYNTHESIS OF 2-AMINOTHIOPHENE DERIVATIVES
    HWANG, KJ
    CHOI, NK
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 1991, 12 (02) : 121 - 122
  • [7] A metal-free one-pot cascade synthesis of highly functionalized biaryl-2-carbaldehydes
    Challa, Chandrasekhar
    Vellekkatt, Jamsheena
    Ravindran, Jaice
    Lankalapalli, Ravi S.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (43) : 8588 - 8592
  • [8] A green chemical approach: a straightforward one-pot synthesis of 2-aminothiophene derivatives via Gewald reaction in deep eutectic solvents
    Shaabani, Ahmad
    Hooshmand, Seyyed Emad
    Afaridoun, Hadi
    MONATSHEFTE FUR CHEMIE, 2017, 148 (04): : 711 - 716
  • [9] A green chemical approach: a straightforward one-pot synthesis of 2-aminothiophene derivatives via Gewald reaction in deep eutectic solvents
    Ahmad Shaabani
    Seyyed Emad Hooshmand
    Hadi Afaridoun
    Monatshefte für Chemie - Chemical Monthly, 2017, 148 : 711 - 716
  • [10] Metal-Free One-Pot Oxidative Amidation of Aldoses with Functionalized Amines
    Colombeau, Ludovic
    Traore, Tenin
    Compain, Philippe
    Martin, Olivier R.
    JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (21): : 8647 - 8650
12345