Metal-Free Synthesis of 2-Benzylideneindolin-3-ones via a Nucleophilic/Rearrangement/Azide-Alkene Cascade Reaction

被引：0
作者：
Tang, Quan [1 ]
Huang, Sheng-Chao [4 ]
Wang, Hua [1 ]
Long, Tianyu [1 ,2 ]
Kong, Han-Han [1 ]
Yang, Qing-Qing [1 ]
Huang, Nianyu [3 ]
Wang, Long [1 ,4 ]
机构：
[1] China Three Gorges Univ, Coll Mat & Chem Engn, Key Lab Inorgan Nonmetall Crystalline & Energy Con, Yichang 443002, Hubei, Peoples R China
[2] China Three Gorges Univ, Coll Hydraul & Environm Engn, Yichang 443002, Hubei, Peoples R China
[3] China Three Gorges Univ, Coll Biol & Pharmaceut Sci, Hubei Key Lab Nat Prod Res & Dev, Yichang 443002, Hubei, Peoples R China
[4] Hubei Three Gorges Labratory, Yichang 443007, Hubei, Peoples R China
来源：
SYNLETT | 2025年 / 36卷 / 04期
基金：
美国国家科学基金会; 中国博士后科学基金;
关键词：
metal-free synthesis; benzylideneindolinones; azidobenzaldehydes; terminal alkynes; azide-alkene cycloaddition; cascade reaction; AZIDE-TETHERED ALKYNES; EXPEDITIOUS SYNTHESIS; PROPARGYLIC ALCOHOLS; VINYL AZIDES; ARYL AZIDES; ACCESS; CYCLIZATION; DERIVATIVES; INDIRUBINS; ANNULATION;
D O I：
10.1055/a-2341-9185
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A metal-free synthesis of 2-benzylideneindolin-3-ones through a formal [4+1] annulation from o -azidobenzaldehydes and terminal alkynes has been developed. The method features operational simplicity, mild reaction conditions, and ready availability of starting materials. A broad range of 2-benzylideneindolin-3-ones were prepared in moderate to excellent yields. Mechanistic studies indicated that the reaction might proceed through a nucleophilic addition/rearrangement/azide-alkene cycloaddition pathway to produce 2-benzylideneindolin-3-ones.
引用
收藏
页码：341 / 346
页数：6
相关论文
共 89 条
  • [1] Unexpected cyclization of ortho-nitrochalcones into 2-alkylideneindolin-3-ones
    Aksenov, Nicolai A.
    Aksenov, Dmitrii A.
    Arutiunov, Nikolai A.
    Aksenova, Daria S.
    Aksenov, Alexander, V
    Rubin, Michael
    [J]. RSC ADVANCES, 2020, 10 (31) : 18440 - 18450
  • [2] A convergent formal [4+2] cycloaddition of 1,6-diynes and benzyl azides: construction of spiro-polyheterocycles
    Bao, Ming
    Lu, Wei
    Su, Han
    Qiu, Lihua
    Xu, Xinfang
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (17) : 3258 - 3265
  • [3] Transformations of 1-amino-2-(3-hydroxyalk-1-ynyl)-9,10-anthraquinones in the presence of amines
    Barabanov, II
    Fedenok, LG
    Polyakov, NE
    Shvartsberg, MS
    [J]. RUSSIAN CHEMICAL BULLETIN, 2001, 50 (09) : 1663 - 1667
  • [4] A short synthetic route to (+)-austamide, (+)-deoxyisoaustamide, and (+)-hydratoaustamide from a common precursor by a novel palladium-mediated indole→dihydroindoloazocine cyclization
    Baran, PS
    Corey, EJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (27) : 7904 - 7905
  • [5] A Bu4N[Fe(CO)3(NO)]-Catalyzed Hemetsberger-Knittel Indole Synthesis
    Baykal, Aslihan
    Plietker, Bernd
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (09) : 1145 - 1147
  • [6] Nucleophilic Iron Complexes in Proton-Transfer Catalysis: An Iron-Catalyzed Dimroth Cyclocondensation
    Baykal, Aslihan
    Zhang, Dihan
    Knelles, Jakob
    Alt, Isabel T.
    Plietker, Bernd
    [J]. CHEMISTRY-AN ASIAN JOURNAL, 2019, 14 (17) : 3003 - 3010
  • [7] Azide trapping of metallocarbenes: generation of reactive C-acylimines and domino trapping with nucleophiles
    Bott, Tina M.
    Atienza, Bren Jordan
    West, F. G.
    [J]. RSC ADVANCES, 2014, 4 (60) : 31955 - 31959
  • [8] BUZAS A, 1989, SYNTHESIS-STUTTGART, P458
  • [9] Structural Optimization of Antimycobacterial Azaaurones Towards Improved Solubility and Metabolic Stability
    Campanico, Andre
    Harjivan, Shrika G.
    Freitas, Elisabete
    Serafini, Marco
    Gaspar, M. Manuela
    Capela, Rita
    Gomes, Pedro
    Jordaan, Audrey
    Madureira, Ana M.
    Andre, Vania
    Silva, Andreia B.
    Duarte, M. Teresa
    Portugal, Isabel
    Perdigao, Joao
    Moreira, Rui
    Warner, Digby F.
    Lopes, Francisca
    [J]. CHEMMEDCHEM, 2023, 18 (24)
  • [10] Azaaurones as Potent Antimycobacterial Agents Active against MDR- and XDR-TB
    Campanico, Andre
    Carrasco, Marta P.
    Njoroge, Mathew
    Seldon, Ronnett
    Chibale, Kelly
    Perdigao, Joao
    Portugal, Isabel
    Warner, Digby F.
    Moreira, Rui
    Lopes, Francisca
    [J]. CHEMMEDCHEM, 2019, 14 (16) : 1537 - 1546
123456789