NHC-Mediated Stetter-Aldol and Imino-Stetter-Aldol Domino Cyclization to Naphthalen-1(2H)-ones and Isoquinolines

被引:9
作者
Barman, Debabrata [1 ]
Ghosh, Tanmoy [1 ]
Show, Krishanu [1 ]
Debnath, Sudipto [1 ]
Ghosh, Tapas [2 ]
Maiti, Dilip K. [1 ]
机构
[1] Univ Calcutta, Dept Chem, Kolkata 700009, India
[2] Maulana Abul Kalam Azad Univ Technol, Dept Appl Sci, Haringhata 741249, W Bengal, India
关键词
CATALYZED REACTIONS; ALDEHYDES; CARBENES; MICHAEL; ENALS;
D O I
10.1021/acs.orglett.1c00337
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
N-Heterocyclic carbene-catalyzed tandem Stetteraldol reaction of phthalaldehyde and alpha,beta-unsaturated ketimines has been developed to afford functionalized naphthalen-1(2H)-one derivatives as the formal [4+2] annulation product. Interestingly, the reaction of aldimines led to the formation of isoquinoline derivatives instead of the expected indanone derivatives as a [4+1] annulation product.
引用
收藏
页码:2178 / 2182
页数:5
相关论文
共 57 条
  • [1] The heck reaction as a sharpening stone of palladium catalysis
    Beletskaya, IP
    Cheprakov, AV
    [J]. CHEMICAL REVIEWS, 2000, 100 (08) : 3009 - 3066
  • [2] POLYPHENYLNAPHTHALENES ESPECIALLY 1,4,5,8-TETRAPHENYLNAPHTHALENE
    BERGMANN, ED
    EPSTEIN, S
    BLUMBERG, S
    BRACHA, P
    [J]. TETRAHEDRON, 1964, 20 (02) : 195 - &
  • [3] Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677
  • [4] Intermolecular N-Heterocyclic Carbene Catalyzed Hydroacylation of Arynes
    Biju, Akkattu T.
    Glorius, Frank
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (50) : 9761 - 9764
  • [5] N-Heterocyclic Carbene-Catalyzed Cascade Reaction Involving the Hydroacylation of Unactivated Alkynes
    Biju, Akkattu T.
    Wurz, Nathalie E.
    Glorius, Frank
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (17) : 5970 - +
  • [6] Bischler A., 1893, CHEM BER-RECL, V26, P1903, DOI [DOI 10.1002/CBER.189302602143, 10.1002/cber.189302602143]
  • [7] Organocatalytic umpolung: N-heterocyclic carbenes and beyond
    Bugaut, Xavier
    Glorius, Frank
    [J]. CHEMICAL SOCIETY REVIEWS, 2012, 41 (09) : 3511 - 3522
  • [8] N-Heterocyclic Carbene (NHC)-Catalyzed Intermolecular Hydroacylation of Cyclopropenes
    Bugaut, Xavier
    Liu, Fan
    Glorius, Frank
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (21) : 8130 - 8133
  • [9] N-Heterocyclic-Carbene-Catalyzed Domino Reactions via Two or More Activation Modes
    Chen, Xiang-Yu
    Li, Sun
    Vetica, Fabrizio
    Kumar, Mukesh
    Enders, Dieter
    [J]. ISCIENCE, 2018, 2 : 1 - 26
  • [10] Palladium-catalyzed α-arylation of carbonyl compounds and nitriles
    Culkin, DA
    Hartwig, JF
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (04) : 234 - 245