Synthesis of 3H-Pyrazolo[3,4-c]isoquinolines and Thieno[3,2-c]isoquinolines via Cascade Imination/Intramolecular Decarboxylative Coupling

被引：31
作者：
Pandey, Garima [1 ]
Bhowmik, Subhendu [1 ]
Batra, Sanjay [1 ,2 ]
机构：
[1] CSIR Cent Drug Res Inst, Med & Proc Chem Div, Lucknow 226031, Uttar Pradesh, India
[2] Acad Sci & Innovat Res, New Delhi, India
来源：
ORGANIC LETTERS | 2013年 / 15卷 / 19期
关键词：
HETEROAROMATIC CARBOXYLIC-ACIDS; BIARYL SYNTHESIS; AROMATIC CARBOXYLATES; DIRECT ARYLATION; TRANSFORMATIONS; PALLADATION;
D O I：
10.1021/ol4023722
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A general approach for the synthesis of 3H-pyrazolo[3,4-c]isoquinolines and thieno[3,2-c]isoquinolines Is described involving the implementation of a cascade imination/intramolecular decarboxylative coupling between potassium 2"amino(hetero)benzoates and 2-haloarylaldehydes. The reactions of pyrazole-based substrates require a Pd-Cu bimetallic system for superior yields whereas the thienyl-based substrates afford the products in excellent yields with a Pd-catalyst only.
引用
收藏
页码：5044 / 5047
页数：4
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  • [1] ANAND NK, 2005, Patent No. 2005009389
  • [2] Synthesis of biaryls via decarboxylative Pd-catalyzed cross-coupling reaction
    Becht, Jean-Michel
    Catala, Cedric
    Le Drian, Claude
    Wagner, Alain
    [J]. ORGANIC LETTERS, 2007, 9 (09) : 1781 - 1783
  • [3] Pd-Catalysed Direct 5-Arylation of 1-Methylpyrazole with Aryl Bromides
    Beladhria, Anissa
    Beydoun, Kassem
    Ben Ammar, Hamed
    Ben Salem, Ridha
    Doucet, Henri
    [J]. SYNTHESIS-STUTTGART, 2011, (16): : 2553 - 2560
  • [4] Substituent-Guided Switch between CH Activation and Decarboxylative Cross-Coupling during Palladium/Copper-Catalyzed Cascade Reactions of 2-Aminobenzoates with 2-Haloarylaldehydes
    Bhowmik, Subhendu
    Pandey, Garima
    Batra, Sanjay
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (32) : 10487 - 10491
  • [5] Palladium-Catalyzed Decarboxylative Cross-Coupling Reaction Between Heteroaromatic Carboxylic Acids and Aryl Halides
    Bilodeau, Francois
    Brochu, Marie-Christine
    Guimond, Nicolas
    Thesen, Kris H.
    Forgione, Pat
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (05) : 1550 - 1560
  • [6] A versatile synthesis of pyrazolo [3,4-c] isoquinoline derivatives by reaction of 4-aryl-5-aminopyrazoles with aryl/heteroaryl aldehydes:: the effect of the heterocycle on the reaction pathways
    Bogza, SL
    Kobrakov, KI
    Malienko, AA
    Perepichka, IF
    Sujkov, SY
    Bryce, MR
    Lyubchik, SB
    Batsanov, AS
    Bogdan, NM
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (05) : 932 - 940
  • [7] Coghlan R.D., 2006, WO Patent, Patent No. [2006069182, 2006069182 A2]
  • [8] CORNELLA J, 2010, CHEM COMMUN, P8276
  • [9] Decarboxylative Carbon-Carbon Bond-Forming Transformations of (Hetero)aromatic Carboxylic Acids
    Cornella, Josep
    Larrosa, Igor
    [J]. SYNTHESIS-STUTTGART, 2012, 44 (05): : 653 - 676
  • [10] Carboxylates as sources of carbon nucleophiles and electrophiles: comparison of decarboxylative and decarbonylative pathways
    Dzik, Wojciech I.
    Lange, Paul P.
    Goossen, Lukas J.
    [J]. CHEMICAL SCIENCE, 2012, 3 (09) : 2671 - 2678
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