Effective and Transition-Metal-Free Construction of Disubstituted, Trisubstituted 1,2,3-NH-Triazoles and Triazolo Pyridazine via Intermolecular 1,3-Dipolar Cycloaddition Reaction

被引：23
|
作者：
Swarup, Hassan. A. [1 ]
Mantelingu, Kemparajegowda Kempegowda [1 ]
Rangappa, Kanchugarkoppal. S. [1 ]
机构：
[1] Univ Mysore, Dept Studies Chem, Mysuru 570006, Karnataka, India
来源：
CHEMISTRYSELECT | 2018年 / 3卷 / 02期
关键词：
1,3-Dipolar cycloaddition reactions; 4,5-Disubstituted 1,2,3-NH-Triazoles; DMSO; Iodine; NaN3; C-H FUNCTIONALIZATION; SODIUM-AZIDE; ONE-POT; TERMINAL ALKYNES; TANDEM APPROACH; FACILE; DERIVATIVES; 4-ARYL-NH-1,2,3-TRIAZOLES; NITROALKANES; CATALYSIS;
D O I：
10.1002/slct.201702547
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An interesting approach for synthesis of disubstituted-1,2,3-(NH) triazoles from easily available raw materials and reagents like substituted acetophenones, iodine, DMSO and NaN3 via intermolecular 1,3-dipolar cycloaddition reaction. Trisubstituted triazoles and its corresponding triazolo pyridazine could be made easily using this method. These are key intermediates for poly benzodithiophene triazole (PBnDT-TAZ) for solar cells and 1-benzyl-1H-4,5-dibenzoyl-1,2,3-triazole (BDBT) for corrosion inhibition.
引用
收藏
页码：703 / 708
页数：6
相关论文
共 50 条
  • [41] One-flask synthesis of 1,3,5-trisubstituted 1,2,4-triazoles from nitriles and hydrazonoyl chlorides via 1,3-dipolar cycloaddition
    Wang, Li-Ya
    Tsai, Henry J.
    Lin, Hui-Yi
    Kaneko, Kimiyoshi
    Cheng, Fen-Ying
    Shih, Hsin-Siao
    Wong, Fung Fuh
    Huang, Jiann-Jyh
    [J]. RSC ADVANCES, 2014, 4 (27): : 14215 - 14220
  • [42] Synthesis of some 1,2,4-Triazolyl-1,2,3-Triazole Derivatives: (1,3-Dipolar Cycloaddition Reaction)
    Abu-Orabi, Sultan T.
    Abu-Naaj, Nuha A.
    Klaib, Sami
    Al-Momani, Lo'ay
    Jibril, Ibrahim
    [J]. JORDAN JOURNAL OF CHEMISTRY, 2008, 3 (04) : 337 - 347
  • [43] 1,2,3-triazole formation under mild conditions via 1,3-dipolar cycloaddition of acetylenes with azides
    Katritzky, AR
    Zhang, YM
    Singh, SK
    [J]. HETEROCYCLES, 2003, 60 (05) : 1225 - 1239
  • [44] Efficient and rapid synthesis of regioselective functionalized potassium 1,2,3-triazoletrifluoroborates via 1,3-dipolar cycloaddition
    Bolla, Krishnavenu
    Kim, Taejung
    Song, Jung Ho
    Lee, Seokjoon
    Ham, Jungyeob
    [J]. TETRAHEDRON, 2011, 67 (31) : 5556 - 5563
  • [45] Synthesis and characterization of new 1,4 and 1,5-disubstituted glucopyranosyl 1,2,3-triazole by 1,3-dipolar cycloaddition
    El Moncef, Abdelkarim
    El Hadrami, El Mestafa
    Ben-Tama, Abdeslem
    Ramirez de Arellano, Carmen
    Zaballos-Garcia, Elena
    Stiriba, Salah-Eddine
    [J]. JOURNAL OF MOLECULAR STRUCTURE, 2009, 929 (1-3) : 6 - 9
  • [46] Organocatalytic 1,3-Dipolar Cycloaddition Reaction of β-Keto Amides with Azides - Direct Access to 1,4,5-Trisubstituted 1,2,3-Triazole-4-carboxamides
    Zhou, Xiao
    Xu, Xianhong
    Liu, Kun
    Gao, Hua
    Wang, Wei
    Li, Wenjun
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (10) : 1886 - 1890
  • [47] Preparation of 1,4-disubstituted-1,2,3-triazolo ribonucleosides by Na2CuP2O7 catalyzed azide-alkyne 1,3-dipolar cycloaddition
    Elayadi, Hanane
    Mesnaoui, Mohamed
    Korba, Brent E.
    Smietana, Michael
    Vasseur, Jean Jacques
    Secrist, John A.
    Lazrek, Hassan B.
    [J]. ARKIVOC, 2012, : 76 - 89
  • [48] Organocatalytic 1,3-dipolar [3+3] cycloaddition reaction of 1,2-cyclohexanedione with azides: direct access to highly substituted 1,2,3-triazoles
    Xu, Xianhong
    Shi, Zhenyan
    Li, Wenjun
    [J]. NEW JOURNAL OF CHEMISTRY, 2016, 40 (08) : 6559 - 6563
  • [49] 1,3-Dipolar cycloaddition reactions of enaminones and azides: Synthesis of 4-acyl-1,2,3-triazoles and mechanistic studies
    Gaspar, Francisco V.
    Azevedo, Marcelo F. M. F.
    Carneiro, Leonardo S. A.
    Ribeiro, Samuel B.
    Esteves, Pierre M.
    Buarque, Camilla D.
    [J]. TETRAHEDRON, 2022, 120
  • [50] Supported NHC-Benzimi@Cu Complex as a Magnetically Separable and Reusable Catalyst for the Multicomponent and Click Synthesis of 1,4-Disubstituted 1,2,3-Triazoles via Huisgen 1,3-Dipolar Cycloaddition
    Pawar, Arvind
    Gajare, Shivanand
    Jagdale, Ashutosh
    Patil, Sandip
    Chandane, Wilson
    Rashinkar, Gajanan
    Patil, Suresh
    [J]. CATALYSIS LETTERS, 2022, 152 (06) : 1854 - 1868
12345