One-Pot Synthesis of 2,3,5-Trisubstituted Thiophenes through Three-Component Assembly of Arylacetaldehydes, Elemental Sulfur, and 1,3-Dicarbonyls

被引:49
|
作者
Wang, Zilong [1 ]
Qu, Zhonghua [1 ]
Xiao, Fuhong [1 ]
Huang, Huawen [1 ]
Deng, Guo-Jun [1 ,2 ,3 ]
机构
[1] Xiangtan Univ, Key Lab Environm Friendly Chem & Applicat, Key Lab Green Organ Synth & Applicat Hunan Prov, Minist Educ,Coll Chem, Xiangtan 411105, Peoples R China
[2] Chinese Acad Sci, Beijing Natl Lab Mol Sci, Inst Chem, Beijing 100190, Peoples R China
[3] Chinese Acad Sci, CAS Key Lab Mol Recognit & Funct, Inst Chem, Beijing 100190, Peoples R China
基金
中国国家自然科学基金;
关键词
Thiophenes; arylacetaldehydes; 1,3-dicarbonyls; elemental sulfur; one-pot; METAL-FREE CONDITIONS; C-H FUNCTIONALIZATION; REGIOSELECTIVE SYNTHESIS; MULTICOMPONENT REACTIONS; BOND FORMATION; TETRASUBSTITUTED THIOPHENES; BETA-KETOTHIOAMIDES; MOLECULAR-IODINE; KEY INTERMEDIATE; IN-SITU;
D O I
10.1002/adsc.201701332
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The three-component reaction for the synthesis of 2-arylthiophenes has been developed. Easily available arylacetaldehydes, 1,3-dicarbonyls, and elemental sulfur were directly assembled through cascade condensation/ annulation under base conditions. The present protocol provides a facile entry to 2,3,5-trisubstituted thiophenes with moderate to excellent yields and good functional group tolerance.
引用
收藏
页码:796 / 800
页数:5
相关论文
共 50 条
  • [1] Selective Formation of 2,3,5-Trisubstituted Furans from 1,3-Dicarbonyls and Hydroxyketones
    Yan, Wanying
    Shou, Jiaru
    Qin, Wenyi
    Mo, Jiayu
    Huang, Huawen
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (22) : 4014 - 4020
  • [2] One-Pot, Three-Component Approach to the Synthesis of 3,4,5-Trisubstituted Pyrazoles
    Kamal, Ahmed
    Sastry, K. N. Visweswara
    Chandrasekhar, D.
    Mani, Geeta Sai
    Adiyala, Praveen Reddy
    Nanubolu, Jagadeesh Babu
    Singarapu, Kiran Kumar
    Maurya, Ram Awatar
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (09): : 4325 - 4335
  • [3] Reaction between Chalcones, 1,3-Dicarbonyl Compounds, and Elemental Sulfur: A One-Pot Three-Component Synthesis of Substituted Thiophenes
    Adib, Mehdi
    Rajai-Daryasarei, Saideh
    Pashazadeh, Rahim
    Jahani, Mehdi
    Amanlou, Massoud
    SYNLETT, 2018, 29 (12) : 1583 - 1588
  • [4] Synthesis of highly functionalized thiophenes by three-component and one-pot reaction
    Hassanabadi, Alireza
    Hosseini-Tabatabaei, Mohammad R.
    JOURNAL OF SULFUR CHEMISTRY, 2012, 33 (03) : 273 - 277
  • [5] User-friendly stereoselective one-pot access to 1,4-diazepane derivatives by a cyclodehydrative three-component reaction with 1,3-dicarbonyls
    Sotoca, Enrique
    Allais, Christophe
    Constantieux, Thierry
    Rodriguez, Jean
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (09) : 1911 - 1920
  • [6] One-Pot, Three-Component Synthesis of 1,4,5-Trisubstituted 1,2,3-Triazoles Starting from Primary Alcohols
    Jin, Guanyi
    Zhang, Jian
    Fu, Dan
    Wu, Jingjing
    Cao, Song
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (28) : 5446 - 5449
  • [7] Ferric oxide nanocatalyst: synthesis, characterization, and application in the one-pot three-component synthesis of 3,4,5-trisubstituted isoxazole derivatives
    Totre, Ganesh
    Shinde, Dnyaneshwar
    Shirsath, Sachin
    Patil, Prakash
    Kulkarni, Pramod
    MONATSHEFTE FUR CHEMIE, 2024, 155 (06): : 631 - 641
  • [8] Ferric oxide nanocatalyst: synthesis, characterization, and application in the one-pot three-component synthesis of 3,4,5-trisubstituted isoxazole derivatives
    Ganesh Totre
    Dnyaneshwar Shinde
    Sachin Shirsath
    Prakash Patil
    Pramod Kulkarni
    Monatshefte für Chemie - Chemical Monthly, 2024, 155 : 631 - 641
  • [9] A novel and facile synthesis of 114,5-trisubstituted 1,2,3-triazoles from benzylic alcohols through a one-pot, three-component system
    Gonzalez-Calderon, Davir
    Santillan-Iniesta, Itzel
    Gonzalez-Gonzalez, Carlos A.
    Fuentes-Benites, Aydee
    Gonzalez-Romero, Carlos
    TETRAHEDRON LETTERS, 2015, 56 (03) : 514 - 516
  • [10] One-Pot Coupling-Cyclization-Alkylation Synthesis of 1,2,5-Trisubstituted 7-Azaindoles in a Consecutive Three-component Fashion
    Lessing, Timo
    Mueller, Thomas J. J.
    SYNLETT, 2017, 28 (14) : 1743 - 1747