Facile One-Pot Assembly of Imidazotriazolobenzodiazepines via Indium(III)-Catalyzed Multicomponent Reactions

被引：64
|
作者：
Nguyen, Huy H. [1 ]
Palazzo, Teresa A. [1 ]
Kurth, Mark J. [1 ]
机构：
[1] Univ Calif Davis, Dept Chem, Davis, CA 95616 USA
来源：
ORGANIC LETTERS | 2013年 / 15卷 / 17期
基金：
美国国家卫生研究院;
关键词：
SUBSTITUTED IMIDAZOLES; BIOLOGICAL EVALUATION; CYCLOADDITION; DERIVATIVES; EFFICIENT; INHIBITORS; AGENTS; ROUTE;
D O I：
10.1021/ol402045h
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An operationally simple, one-pot multicomponent reaction has been developed for the assembly of 9H-benzo[f]imidazo[1,2-d][1,2,3]triazolo[1,5-a][1,4]diazepines adorned with three diversification points via an atom-economical transformation incorporating alpha-diketones, o-azidobenzaldehydes, propargylic amines, and ammonium acetate. This process involves tandem InCI3-catalyzed cyclocondensation and intramolecular azide-alkyne 1,3-dipolar cycloaddition reactions; optimization data, substrate scope, and mechanistic insights are discussed.
引用
收藏
页码：4492 / 4495
页数：4
相关论文
共 50 条
  • [41] Green preparation of new pyrimidine triazole derivatives via one-pot multicomponent reactions of guanidine
    Hezarcheshmeh, Nasrin Karami
    Godarzbod, Farideh
    Abdullah, Media Noori
    Hossaini, Zinatossadat
    MOLECULAR DIVERSITY, 2024, 28 (01) : 217 - 228
  • [42] A one-pot multicomponent synthesis of polysubstituted thiophenes via the reactions of an isocyanide, α-haloketones, and β-ketodithioesters in water
    Moghaddam, Firouz MatIoubi
    Khodabakhshi, Mohammad Reza
    Latifkar, Arash
    TETRAHEDRON LETTERS, 2014, 55 (06) : 1251 - 1254
  • [43] Green preparation of new pyrimidine triazole derivatives via one-pot multicomponent reactions of guanidine
    Nasrin Karami Hezarcheshmeh
    Farideh Godarzbod
    Media Noori Abdullah
    Zinatossadat Hossaini
    Molecular Diversity, 2024, 28 : 217 - 228
  • [44] Green Synthesis and Theoretical Study of New Imidazopyrimidine Derivatives via One-Pot Multicomponent Reactions
    Ezzatzadeh, Elham
    Mohammadi, Marziyeh
    Hossaini, Zinatossadat
    Khandan, Samira
    CHEMISTRYSELECT, 2023, 8 (39):
  • [45] Convenient one-pot synthesis of multisubstituted tetrahydropyrimidines via catalyst-free multicomponent reactions
    Zhang, Min
    Jiang, Huanfeng
    Liu, Hailing
    Zhu, Qiuhua
    ORGANIC LETTERS, 2007, 9 (21) : 4111 - 4113
  • [46] A facile one-pot synthesis of 7-triethylsilylbaccatin III
    Baloglu, E
    Miller, ML
    Cavanagh, EE
    Marien, TP
    Roller, EE
    Chari, RVJ
    SYNLETT, 2005, (05) : 817 - 818
  • [47] ONE-POT SYNTHESIS OF TRISUBSTITUTED PYRAZOLES VIA MULTICOMPONENT APPROACH
    Santhosh, P.
    Chunduru, V. S. R.
    Rao, V. Rajeswar
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2011, 47 (04) : 448 - 451
  • [48] One-pot synthesis of trisubstituted pyrazoles via multicomponent approach
    P. Santhosh
    V. S. R. Chunduru
    V. Rajeswar Rao
    Chemistry of Heterocyclic Compounds, 2011, 47 : 448 - 451
  • [49] Novel Synthesis of Functionalized Bis(Benzo-Heterocyclic Amine) Derivatives via Copper-Catalyzed One-Pot Multicomponent Reactions
    Nematpour, Manijeh
    CHEMISTRYSELECT, 2024, 9 (27):
  • [50] Multicomponent reactions of ammonium thiocyanate, acyl chlorides, alkyl bromides, and enaminones: A facile one-pot synthesis of thiophenes
    Hossaini, Zinatossadat
    Rostami-Charati, Faramarz
    Soltani, Samira
    Mirzaei, Anwar
    Berijani, Kayhaneh
    MOLECULAR DIVERSITY, 2011, 15 (04) : 911 - 916
12345