Lewis acid-catalyzed redox-neutral amination of 2-(3-pyrroline-1-yl)benzaldehydes via intramolecular [1,5]-hydride shift/isomerization reaction

被引:9
|
作者
Jiang, Chun-Huan [1 ,2 ]
Lei, Xiantao [1 ,2 ]
Zhen, Le [1 ,2 ]
Du, Hong-Jin [1 ,2 ]
Wen, Xiaoan [1 ,2 ]
Xu, Qing-Long [1 ,2 ]
Sun, Hongbin [1 ,2 ]
机构
[1] China Pharmaceut Univ, State Key Lab Nat Med, Nanjing 210009, Jiangsu, Peoples R China
[2] China Pharmaceut Univ, Jiangsu Key Lab Drug Discovery Metab Dis, Nanjing 210009, Jiangsu, Peoples R China
来源
基金
中国国家自然科学基金;
关键词
catalysis; C-H activation; hydride-shift; Lewis acid; redox reaction; H BOND FUNCTIONALIZATION; CYCLIC AMINALS; ACTIVATION; CHEMISTRY; ARYLATION; PYRROLES; COMPLEX;
D O I
10.3762/bjoc.10.306
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Lewis acid-catalyzed redox-neutral amination of 2-(3-pyrroline-1-yl) benzaldehydes via intramolcular [1,5]-hydride shift/isomerization reaction has been realized, using the inherent reducing power of 3-pyrrolines. A series of N-arylpyrrole containing amines are obtained in high yields.
引用
收藏
页码:2892 / 2896
页数:5
相关论文
共 26 条
  • [1] Construction of Oxadiazepines via Lewis Acid-Catalyzed Tandem 1,5-Hydride Shift/Cyclization
    Chang, Yong-Zhi
    Li, Ming-Lei
    Zhao, Wen-Feng
    Wen, Xiaoan
    Sun, Hongbin
    Xu, Qing-Long
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (19): : 9620 - 9627
  • [2] Rhodium-Catalyzed Intramolecular Acylation of 2-(Indol-1-yl)-benzoic Acids under Redox-Neutral Conditions
    Suzuki, Hirotsugu
    Takemura, Yosuke
    Matsuda, Takanori
    SYNLETT, 2023, 34 (16) : 1894 - 1898
  • [3] STEROIDS AND SEX-HORMONES .264. LEWIS ACID-CATALYZED REVERSIBLE [1,5]-HYDRIDE SHIFT IN 3,19-EPOXY-STEROIDS
    ACKLIN, G
    GRAF, W
    HELVETICA CHIMICA ACTA, 1980, 63 (08) : 2342 - 2357
  • [4] Approach to N-aryl pyrroles via diphenyl phosphate-catalyzed [1,5]-Hydride shift/isomerization reaction with indoles
    Lei, Xiantao
    Xie, Hong-Yan
    Chen, Si-Yuan
    Teng, Kai-Shun
    Wen, Xiaoan
    Xu, Qing-Long
    Sun, Hongbin
    TETRAHEDRON, 2015, 71 (24) : 4098 - 4101
  • [5] Regioselective synthesis of C-prenylated flavonoids via intramolecular [1,3] or [1,5] shift reaction catalyzed by acidic clays
    Li, Wei
    Shu, Liang
    Liu, Kexiong
    Wang, Qiuan
    TETRAHEDRON LETTERS, 2019, 60 (41)
  • [6] Rearrangement of 2-(4-hydroxyalkyl)-1,3-dioxolanes to 2-hydroxyethyl alkanoic esters by 1,5-hydride shift -: An unprecedented intramolecular redox reaction
    Krohn, K
    Flörke, U
    Höfker, U
    Träubel, M
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 1999, 1999 (12) : 3495 - 3499
  • [7] The Lewis acid-catalyzed Nazarov reaction of 2-(N-methoxycarbonylamino)-1,4-pentadien-3-ones
    Larini, P
    Guarna, A
    Occhiato, EG
    ORGANIC LETTERS, 2006, 8 (04) : 781 - 784
  • [8] Copper-catalyzed intramolecular redox reaction: Asymmetric synthesis of chiral 2-(1H-pyrrol-1-yl)-mandelic acid esters
    Du, Hong-Jin
    Lin, Chao
    Wen, Xiaoan
    Xu, Qing-Long
    TETRAHEDRON, 2018, 74 (52) : 7480 - 7484
  • [9] ACID-CATALYZED INTRAMOLECULAR MICHAEL ADDITION OF 1-ACYL-1'-CINNMOYLFERROCENES - PROOF OF STRUCTURE OF 2-SUBSTITUTED 3-PHENYL[5]FERROCENOPHANE-1,5-DIONES
    ELECKO, P
    SOLCANIO.E
    VIDA, M
    COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1974, 39 (12) : 3684 - 3688
  • [10] Room temperature intramolecular hydro-O-alkylation of aldehydes:: sp3 C-H functionalization via a Lewis acid catalyzed tandem 1,5-hydride transfer/cyclization
    Pastine, SJ
    Sames, D
    ORGANIC LETTERS, 2005, 7 (24) : 5429 - 5431