Synthesis of 1H-Thiopyrano[4,3-c]quinoline Scaffold via One-pot Three-component Cyclization

被引:8
|
作者
Alizadeh, Abdolali [1 ]
Rezaiyehraad, Reza [1 ]
Roosta, Atefeh [1 ]
Halvagar, Mohammad Reza [2 ]
机构
[1] Tarbiat Modares Univ, Dept Chem, POB 14115-175, Tehran, Iran
[2] CCERCI, Pajohesh Blvd,17th Km Tehran Karaj Highway, Tehran 1496813151, Iran
来源
CHEMISTRYSELECT | 2019年 / 4卷 / 41期
关键词
2-chloroquinoline-3-carbaldehyde; phenacyl thiocyanate; 1H-thiopyrano[4; 3-c]quinoline; thiopyranoquinoline; EFFICIENT ONE-POT; MICROWAVE-ASSISTED SYNTHESIS; DOMINO REACTIONS; HETEROCYCLIC-ANALOGS; ANTITUMOR-ACTIVITY; DNA-BINDING; DERIVATIVES; CONSTRUCTION; QUINOLINES; FACILE;
D O I
10.1002/slct.201903019
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A convenient and effective one-pot synthetic method for functionalized 1H-thiopyrano[4,3-c]quinoline scaffold via three-component cyclization is described. This procedure contains the reaction between 2-chloroquinoline-3-carbaldehyde and 2 equivalents of phenacyl thiocyanate in the presence of triethylamine in absolute ethanol at room temperature with good yield. This eco-friendly method has advantages such as reduction of waste, short synthetic procedure, and little amount of required reagents.
引用
收藏
页码:12049 / 12052
页数:4
相关论文
共 50 条
  • [1] Three-component one-pot synthesis of dihydrochromeno[4,3-b]pyrazolo[4,3-e]pyridines
    Sadat-Ebrahimi, Seyed Esmail
    Katebi, Shirin
    Pirali-Hamedani, Morteza
    Moghimi, Setareh
    Yahya-Meymandi, Azadeh
    Mahdavi, Mohammad
    Shafiee, Abbas
    Foroumadi, Alireza
    HETEROCYCLIC COMMUNICATIONS, 2016, 22 (04) : 247 - 250
  • [2] One-Pot Synthesis of Dihydropyrano[2,3-c]chromenes via a Three-Component Reaction in Aqueous Media
    Balalaie, Saeed
    Khazaie, Ahmad
    Ashouriha, Morteza
    COMBINATORIAL CHEMISTRY & HIGH THROUGHPUT SCREENING, 2013, 16 (10) : 845 - 850
  • [3] An Efficient Synthesis of 4H-chromene Derivatives by a One-pot, Three-component Reaction
    Poursattar Marjani, Ahmad
    Ebrahimi Saatluo, Bahman
    Nouri, Fariba
    IRANIAN JOURNAL OF CHEMISTRY & CHEMICAL ENGINEERING-INTERNATIONAL ENGLISH EDITION, 2018, 37 (01): : 149 - 157
  • [4] One-pot three-component synthesis of novel spiroindenoquinoxalines
    Chen, Feiran
    Zheng, Jia
    Huang, Mingming
    Li, Yiqun
    RESEARCH ON CHEMICAL INTERMEDIATES, 2015, 41 (08) : 5545 - 5554
  • [5] Stereoselective, One-Pot, Three-Component Synthesis of 4-Aryltetrahydropyrans from Epoxides via Prins Cyclization Reaction
    Indukuri, Kiran
    Bondalapati, Somasekhar
    Kotipalli, Trimurtulu
    Gogoi, Paramartha
    Saikia, Anil K.
    SYNLETT, 2012, (02) : 233 - 238
  • [6] Synthesis of polycyclic N-heterocyclic compounds via one-pot three-component cyclization strategy
    Alizadeh, Abdolali
    Sanjari, Elham
    Roosta, Atefeh
    Halvagar, Mohammad Reza
    MOLECULAR DIVERSITY, 2021, 25 (04) : 2063 - 2072
  • [7] One-pot three-component regioselective synthesis of C1-functionalised 3-arylbenzo[f]quinoline
    Gattu, Radhakrishna
    Basha, R. Sidick
    Bagdi, Prasanta Ray
    Khan, Abu T.
    RSC ADVANCES, 2016, 6 (14) : 11675 - 11682
  • [8] One-Pot Three-Component Approach to the Synthesis of Polyfunctional Pyrazoles
    Zhang, Guolin
    Ni, Hangcheng
    Chen, Wenteng
    Shao, Jiaan
    Liu, Huan
    Chen, Binhui
    Yu, Yongping
    ORGANIC LETTERS, 2013, 15 (23) : 5967 - 5969
  • [9] Synthesis of novel 4H-pyrimido[1,6-a]pyrimidines via a one-pot three-component condensation
    Xiang, Jinbao
    Li, Hanghang
    Yang, Kai
    Yi, Lang
    Xu, Yongnan
    Dang, Qun
    Bai, Xu
    MOLECULAR DIVERSITY, 2012, 16 (01) : 173 - 181
  • [10] Three-Component One-Pot Approach to Synthesize Benzopyrano[4,3-d]pyrimidines
    Li, Dewen
    Duan, Shudong
    Hu, Youhong
    JOURNAL OF COMBINATORIAL CHEMISTRY, 2010, 12 (06): : 895 - 899