Copper-catalyzed Synthesis of N-alkylated 2-(4-substituted-1H-1,2,3-triazol-1-yl)-1H-indole-3-carbaldehyde by Step-wise and One-pot Three-component Huisgen's 1,3-dipolar Cycloaddition Reaction

被引：4
|
作者：
Avula, Vijay Kumar Reddy [1 ,2 ]
Vallela, Swetha [2 ]
Anireddy, Jaya Shree [2 ]
Chamarthi, Naga Raju [1 ]
机构：
[1] Sri Venkateswara Univ, Dept Chem, Tirupati, Andhra Pradesh, India
[2] Jawaharlal Nehru Technol Univ, IST, Ctr Chem Sci & Technol, Hyderabad, Andhra Pradesh, India
来源：
JOURNAL OF HETEROCYCLIC CHEMISTRY | 2017年 / 54卷 / 06期
关键词：
TRIAZOLE OXINDOLE TROX-1; SMALL-MOLECULE; IN-VIVO; INHIBITORS; CONGENERS;
D O I：
10.1002/jhet.2918
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient method for the synthesis of N-alkylated 2-(4-substituted-1H-1,2,3-triazol-1-yl)-1H-indole-3-carbaldehyde has been developed starting from oxindole and indole using Huisgen's 1,3-dipolar cycloaddition reaction of organic azides to alkynes. The effect of catalysts and solvent on these reactions has been investigated. Among all these conditions, while using CuSO4 center dot 5H(2)O, DMF was found to be the best system for this reaction. It could also be prepared in a one-pot three-component manner by treating equimolar quantities of halides, azides, and alkynes. The Huisgen's 1,3-dipolar cycloaddition reaction was performed using CuSO4 center dot 5H(2)O in DMF with easy work-up procedure.
引用
收藏
页码：3071 / 3076
页数：6
相关论文
共 50 条
  • [1] Synthesis of 3-(1H-1,2,3-Triazol-1-yl)-2-(arylselanyl)pyridines by Copper-Catalyzed 1,3-Dipolar Cycloaddition of 2-(Arylselanyl)-3-azido-pyridines with Terminal Alkynes
    Schumacher, Ricardo F.
    Von Laer, Patrick B.
    Betin, Eduardo S.
    Cargnelutti, Roberta
    Perin, Gelson
    Alves, Diego
    JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2015, 26 (11) : 2298 - 2306
  • [2] One-pot three-component synthesis of substituted 2-(1,2,3-triazol-1-yl) pyrimidines from pyrimidin-2-yl sulfonates, sodium azide and active methylene ketones
    Quan, Zheng-Jun
    Wang, Miao-Miao
    Yang, Liang-Jie
    Da, Yu-Xia
    Zhang, Zhang
    Wang, Xi-Cun
    HETEROCYCLIC COMMUNICATIONS, 2014, 20 (01) : 1 - 4
  • [3] One-pot synthesis of alkyl 3-aryl-2-(4-phenyl-1H-1,2,3-triazol-1-yl)propanoates
    N. T. Pokhodylo
    R. D. Savka
    M. D. Obushak
    Russian Journal of Organic Chemistry, 2017, 53 : 734 - 737
  • [4] One-pot synthesis of alkyl 3-aryl-2-(4-phenyl-1H-1,2,3-triazol-1-yl)propanoates
    Pokhodylo, N. T.
    Savka, R. D.
    Obushak, M. D.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 53 (05) : 734 - 737
  • [5] One-Pot, Three-Component Synthesis of 1-(2-Hydroxyethyl)-1H-1,2,3-triazole Derivatives by Copper-Catalyzed 1,3-Dipolar Cycloaddition of 2-Azido Alcohols and Terminal Alkynes under Mild Conditions in Water
    Sharghi, Hashem
    Hosseini-Sarvari, Mona
    Moeini, Fatemeh
    Khalifeh, Reza
    Beni, Alireza Salimi
    HELVETICA CHIMICA ACTA, 2010, 93 (03) : 435 - 449
  • [6] Copper(I)-Catalyzed Azide-Alkyne Cycloaddition Microwave-Assisted: Preparation of 7-(4-Substituted-1H-1,2,3-Triazol-1-yl)-Fluoroquinolones
    Hernandez-Lopez, Hiram
    Leyva-Ramos, Socorro
    Delia Moncada-Martinez, Rosa
    Adrian Lopez, Jesus
    Cardoso-Ortiz, Jaime
    CHEMISTRYSELECT, 2019, 4 (40): : 11899 - 11902
  • [7] Synthesis of 3′-deoxy-3′-[4-(pyrimidin-1-yl)methyl-1,2,3-triazol-1-yl]thymidine via 1,3-dipolar cycloaddition
    Tourirte, M
    Oulih, T
    Lazrek, HB
    Barascut, JL
    Imbach, JL
    Almasoudi, NA
    NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2003, 22 (11): : 1985 - 1993
  • [8] A one-pot synthesis and 1,3-dipolar cycloaddition of [1,2]dithiolo[4,3-b]indole-3(4H)-thiones
    Konstantinova, Lidia S.
    Lysov, Kirill A.
    Amelichev, Stanislav A.
    Obruchnikova, Natalia V.
    Rakitin, Oleg A.
    TETRAHEDRON, 2009, 65 (11) : 2178 - 2183
  • [9] Synthesis and Antimicrobial Activity of 2-(4-(Hydroxyalkyl)-1H-1,2,3-triazol-1-yl)-N-substituted propanamides
    Kaushik, C. P.
    Luxmi, Raj
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2017, 54 (06) : 3618 - 3625
  • [10] One-pot three-component green synthesis of [1H-(1,2,3-triazol-5-yl)methylidene] heterocycles based on element-substituted propynals
    M. M. Demina
    A. S. Medvedeva
    T. L. H. Nguyen
    T. D. Vu
    L. I. Larina
    Russian Chemical Bulletin, 2017, 66 : 2253 - 2257
12345