Simplified synthesis of 3-(1-arylsulfonylalkyl) indoles and their reaction with Reformatsky reagents

被引:72
作者
Palmieri, Alessandro [1 ]
Petrini, Marino [1 ]
机构
[1] Univ Camerino, Dipartimento Sci Chim, I-62032 Camerino, Italy
关键词
D O I
10.1021/jo062538e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple procedure for the preparation of 3-(1-arylsulfonyl-alkyl) indoles by three-component condensation of indoles, carbonyls, and arenesulfinic acids is presented. The obtained products undergo a Reformatsky reaction leading to alkyl 3-(3-indolyl) alkanoates and (3-indolyl) ketones.
引用
收藏
页码:1863 / 1866
页数:4
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共 33 条
  • [1] A practical synthetic route to functionalized THBCs and oxygenated analogues via intramolecular Friedel-Crafts reactions
    Angeli, Marco
    Bandini, Marco
    Garelli, Andrea
    Piccinelli, Fabio
    Tommasi, Simona
    Umani-Ronchi, Achille
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (17) : 3291 - 3296
  • [2] Practical enantioselective synthesis of β-substituted-β-amino esters
    Awasthi, AK
    Boys, ML
    Cain-Janicki, KJ
    Colson, PJ
    Doubleday, WW
    Duran, JE
    Farid, PN
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (14) : 5387 - 5397
  • [3] Solventless clay-promoted Friedel-Crafts reaction of indoles with α-amido sulfones:: Unexpected synthesis of 3-(1-arylsulfonylalkyl) indoles
    Ballini, Roberto
    Palmieri, Alessandro
    Petrini, Marino
    Torregiani, Elisabetta
    [J]. ORGANIC LETTERS, 2006, 8 (18) : 4093 - 4096
  • [4] A journey across recent advances in catalytic and stereoselective alkylation of indoles
    Bandini, M
    Melloni, A
    Tommasi, S
    Umani-Ronchi, A
    [J]. SYNLETT, 2005, (08) : 1199 - 1222
  • [5] Solid acid-catalysed Michael-type conjugate addition of indoles to electron-poor C=C bonds: Towards high atom economical semicontinuous processes
    Bandini, M
    Fagioli, M
    Umani-Ronchi, A
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (05) : 545 - 548
  • [6] Efficient preparation of 2-indolyl-1-nitroalkane derivatives employing nitroalkenes as versatile Michael acceptors:: New practical linear approach to alkyl 9H-β-Carboline-4-carboxylate
    Bartoli, G
    Bosco, M
    Giuli, S
    Giuliani, A
    Lucarelli, L
    Marcantoni, E
    Sambri, L
    Torregiani, E
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (05) : 1941 - 1944
  • [7] New cascade 2-indolylacyl radical addition-cyclization reactions
    Bennasar, ML
    Roca, T
    Griera, R
    Bosch, J
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (22) : 7547 - 7551
  • [8] An efficient and clean synthesis of bis(indolyl)methanes in a protic solvent at room temperature
    Deb, WL
    Bhuyan, PJ
    [J]. TETRAHEDRON LETTERS, 2006, 47 (09) : 1441 - 1443
  • [9] Dessole G., 2004, SYNLETT, P2374
  • [10] PREPARATION OF THE (R)-ENANTIOMER AND (S)-ENANTIOMER OF 10-HYDROXYMETHYLFURO[3,4-C]-BETA-CARBOLINE-2(10H)ONE, THE FIRST EXAMPLE OF A BENZODIAZEPINE RECEPTOR-LIGAND OF THE BETA-CARBOLINE FAMILY HAVING A STEREOGENIC CENTER
    DUBOIS, L
    DOREY, G
    POTIER, P
    DOOD, RH
    [J]. TETRAHEDRON-ASYMMETRY, 1995, 6 (02) : 455 - 462