Metal-Free Three-Component Assembly of Fully Substituted 1,2,3-Triazoles

被引：16
|
作者：
Ahamad, Shakir [1 ,3 ]
Kumar, Anuj [1 ]
Kant, Ruchir [2 ]
Mohanan, Kishor [1 ,3 ]
机构：
[1] CSIR Cent Drug Res Inst, Med & Proc Chem Div, Lucknow 226031, Uttar Pradesh, India
[2] CSIR Cent Drug Res Inst, Mol & Struct Biol, Lucknow 226031, Uttar Pradesh, India
[3] Acad Sci & Innovat Res, New Delhi, India
来源：
ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 7卷 / 08期
关键词：
cycloaddition; diazomethylsulfones; metal-free synthesis; three-component reactions; triazoles; BESTMANN-OHIRA REAGENT; AZIDE-ALKYNE CYCLOADDITION; ONE-POT SYNTHESIS; REGIOSELECTIVE SYNTHESIS; CLICK CHEMISTRY; 1,3-DIPOLAR CYCLOADDITION; CATALYZED TRANSANNULATION; REGIOSPECIFIC SYNTHESIS; N-TOSYLHYDRAZONES; RAPID SYNTHESIS;
D O I：
10.1002/ajoc.201800340
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A practical domino three-component protocol involving aldehydes, amines, and alpha-diazo-beta-ketosulfones provides efficient access to fully substituted 1,2,3-triazoles. The process proceeds through a tandem Schiff-base formation and 1,3-dipolar cycloaddition to generate a key sulfonyltriazoline intermediate, which subsequently undergoes an oxidative aromatization with the aid of air or iodine. The three-component protocol obviates the need of expensive metal catalysts, proceeds under mildly basic conditions, and tolerates a wide range of synthetically useful (hetero)aryl and aliphatic aldehydes, and functionalized amines.
引用
收藏
页码：1698 / 1703
页数：6
相关论文
共 50 条
  • [41] Green synthesis of substituted 1,2,3-triazoles (student)
    Raikevitch, Cathleen
    Kellen-Yuen, Cynthia
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 231
  • [42] Boron-substituted 1,2,3-triazoles (microreview)
    Pokhodylo, Nazariy T.
    Pitkovych, Khryestyna Ye.
    [J]. CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2021, 57 (7-8) : 737 - 739
  • [43] SYNTHESIS OF PROPENYL-SUBSTITUTED 1,2,3-TRIAZOLES
    SHATALOV, GV
    KRIVTSOV, VP
    MIKHANTYEV, BI
    [J]. KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1981, (04): : 565 - 565
  • [44] Organocatalytic routes toward substituted 1,2,3-triazoles
    John, Jubi
    Thomas, Joice
    Dehaen, Wim
    [J]. CHEMICAL COMMUNICATIONS, 2015, 51 (54) : 10797 - 10806
  • [45] Selective Synthesis of Functionally Substituted 1,2,3-Triazoles
    Golobokova, T. V.
    Proidakov, A. G.
    Kizhnyaev, V. N.
    [J]. RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 56 (03) : 446 - 453
  • [46] Fluorinated 1,2,3-Triazoles: Terra Incognita in 1,2,3-Triazoles Chemistry
    Pokhodylo, Nazariy
    Levchenko, Kostiantyn
    Obushak, Mykola
    [J]. CHEMISTRYSELECT, 2024, 9 (04):
  • [47] CARBOHYDRATE DERIVATIVES OF 1-SUBSTITUTED 1,2,3-TRIAZOLES
    KHADEM, HE
    SHABAN, MAE
    [J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1967, (06): : 519 - &
  • [48] Synthesis of β-triazolylenones via metal-free desulfonylative alkylation of N-tosyl-1,2,3-triazoles
    Pati, Soumyaranjan
    Almeida, Renata G.
    da Silva Junior, Eufranio N.
    Namboothiri, Irishi N. N.
    [J]. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2021, 17 : 762 - 770
  • [49] Metal-free, highly regioselective sulfonylation of NH-1,2,3-triazoles with sodium sulfinates and thiosulfonates
    Reddy, Raju Jannapu
    Shankar, Angothu
    Waheed, Md
    Nanubolu, Jagadeesh Babu
    [J]. TETRAHEDRON LETTERS, 2018, 59 (21) : 2014 - 2017
  • [50] Computational studies of the metal-free [3+2] cycloaddition reaction of azide with enaminone for the synthesis of 1,2,3-triazoles
    Badawi, Mohammad Abd Al-Hakim
    Dagher, Maram
    Alzahrani, Abdullah Yahya Abdullah
    Khairbek, Ali A.
    Thomas, Renjith
    [J]. New Journal of Chemistry, 2024, 49 (01) : 291 - 301
12345