Metal-free cascade reactions of aziridines with arylalkynes and aryldiazoniums: facile access to arylazopyrrolines

被引:10
作者
Rong, Jing [1 ]
Jiang, Hao [1 ]
Wang, Sijing [1 ]
Su, Zhenni [1 ]
Wang, Huiyan [1 ]
Tao, Chuanzhou [1 ]
机构
[1] Jiangsu Ocean Univ, Sch Chem Engn, Lianyungang 222005, Peoples R China
基金
中国国家自然科学基金;
关键词
MUTUAL AZO PRODRUGS; 2,3-DIHYDROPYRROLES; DESIGN; AGENTS; ACID; DERIVATIVES; CYCLIZATION; INHIBITORS; ASSEMBLIES; COMPLEXES;
D O I
10.1039/d0ob00346h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel and facile approach to synthesize arylazopyrroline scaffolds via metal-free cascade reactions of aziridines with arylalkynes and aryldiazoniums has been developed, providing access to a variety of 4-arylazo-2-pyrrolines in a highly concise fashion. This efficient process, which can be performed at the gram scale, enjoys operational simplicity and mild and metal-free conditions.
引用
收藏
页码:3149 / 3157
页数:9
相关论文
共 49 条
  • [1] BENZENEDIAZONIUM IONS - STRUCTURE, COMPLEXATION, AND REACTIVITY
    ANDERSON, LM
    BUTLER, AR
    MCINTOSH, AS
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1987, (09): : 1239 - 1241
  • [2] From metal complexes to metallosupramolecular polymers via polycondensation: Synthesis, structure and electrochromic properties of Co(III)- and Fe(III)-based metallosupramolecular polymers with aromatic azo ligands
    Bandyopadhyay, Anasuya
    Higuchi, Masayoshi
    [J]. EUROPEAN POLYMER JOURNAL, 2013, 49 (06) : 1688 - 1697
  • [3] Application of host-guest chemistry in nanotube-based device fabrication:: Photochemically controlled immobilization of azobenzene nanotubes on patterned α-CD monolayer/Au substrates via molecular recognition
    Banerjee, IA
    Yu, LT
    Matsui, H
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (32) : 9542 - 9543
  • [4] Iodine-Catalyzed Diazenylation with Arylhydrazine Hydrochlorides in Air
    Barak, Dinesh S.
    Dighe, Shashikant U.
    Avasthi, Ilesha
    Batra, Sanjay
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (07) : 3537 - 3546
  • [5] Total syntheses of ningalin A, lamellarin O, lukianol A, and permethyl storniamide A utilizing heterocyclic azadiene Diels-Alder reactions
    Boger, DL
    Boyce, CW
    Labroli, MA
    Sehon, CA
    Jin, Q
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (01) : 54 - 62
  • [6] The role of natural product chemistry in drug discovery
    Butler, MS
    [J]. JOURNAL OF NATURAL PRODUCTS, 2004, 67 (12): : 2141 - 2153
  • [7] Tuning Azoheteroarene Photoswitch Performance through Heteroaryl Design
    Calbo, Joaquin
    Weston, Claire E.
    White, Andrew J. P.
    Rzepa, Henry S.
    Contreras-Garcia, Julia
    Fuchter, Matthew J.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (03) : 1261 - 1274
  • [8] Ionic Liquid Promoted Diazenylation of N-Heterocyclic Compounds with Aryltriazenes under Mild Conditions
    Cao, Dawei
    Zhang, Yonghong
    Liu, Chenjiang
    Wang, Bin
    Sun, Yadong
    Abdukadera, Ablimit
    Hu, Haiyan
    Liu, Qiang
    [J]. ORGANIC LETTERS, 2016, 18 (09) : 2000 - 2003
  • [9] L-Lysine Pro-Prodrug Containing trans-Ferulic Acid for 5-Amino Salicylic Acid Colon Delivery: Synthesis, Characterization and in Vitro Antioxidant Activity Evaluation
    Cassano, Roberta
    Trombino, Sonia
    Cilea, Alessia
    Ferrarelli, Teresa
    Muzzalupo, Rita
    Picci, Nevio
    [J]. CHEMICAL & PHARMACEUTICAL BULLETIN, 2010, 58 (01) : 103 - 105
  • [10] Synthesis, kinetic studies and pharmacological evaluation of mutual azo prodrugs of 5-aminosalicylic acid for colon-specific drug delivery in inflammatory bowel disease
    Dhaneshwar, Suneela S.
    Gairola, Neha
    Kandpal, Mini
    Vadnerkar, Gaurav
    Bhatt, Lokesh
    Rathi, Badal
    Kadam, S. S.
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (10) : 3922 - 3929