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] 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
  • [3] 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
  • [4] 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
  • [5] 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
  • [6] Synthesis of Benzo[b]thiophenes through Rhodium-Catalyzed Three-Component Reaction using Elemental Sulfur
    Moon, Sanghun
    Kato, Moena
    Nishii, Yuji
    Miura, Masahiro
    ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (08) : 1669 - 1673
  • [7] Direct synthesis of 2,3,5-trisubstituted pyrroles via copper-mediated one-pot multicomponent reaction
    He, Jian-Ping
    Zhan, Zhen-Zhen
    Luo, Nan
    Zhang, Ming-Ming
    Huang, Guo-Sheng
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (48) : 9831 - 9835
  • [8] Novel synthesis of 1,4,5-trisubstituted 1,2,3-triazoles via a one-pot three-component reaction of boronic acids, azide, and active methylene ketones
    Zhang, Jian
    Jin, Guanyi
    Xiao, Senhan
    Wu, Jingjing
    Cao, Song
    TETRAHEDRON, 2013, 69 (10) : 2352 - 2356
  • [9] Facile one-pot three-component strategy for the synthesis of 2-amino-4-arylthiazoles via elemental sulfur source
    Liang, Xiao-Ping
    Luo, Min
    Kang, Li
    Tang, Long-Xing
    Liang, Qing
    Liu, Yuan-Lin
    Yang, Zi
    Zhang, Chun-Tao
    Peng, Cai-Yun
    Fu, Rong-Geng
    TETRAHEDRON LETTERS, 2022, 100
  • [10] One-pot parallel synthesis of 1,3,5-trisubstituted 1,2,4-triazoles
    Radchenko, Dmytro S.
    Naumchyk, Vasyl S.
    Dziuba, Igor
    Kyrylchuk, Andrii A.
    Gubina, Kateryna E.
    Moroz, Yurii S.
    Grygorenko, Oleksandr O.
    MOLECULAR DIVERSITY, 2022, 26 (02) : 993 - 1004