Gold-catalyzed C-3-alkylation of 7-azaindoles through Michael-type addition to α,β-enones

被引:32
作者
Alfonsi, Maria [1 ]
Arcadi, Antonio [1 ]
Bianchi, Gabriele [1 ]
Marinelli, Fabio [1 ]
Nardini, Antonella [1 ]
机构
[1] Univ Aquila, Dipartimento Chim Ingn Chim & Mat, I-67010 Laquila, Italy
关键词
gold; catalysis; 7-azaindoles; enones; conjugate addition; alkylation;
D O I
10.1002/ejoc.200500998
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Au-III-catalyzed reactions of 7-azaindole derivatives with alpha,beta-enones are described. Factors that can direct the C-3-versus N-1-alkylation reaction on the 7-azaindole nucleus are explored. The Au-III-catalyzed reaction of 7-azaindole with P-unsubstituted alpha,beta-enones afforded 1-substituted 7-azaindoles through an aza-Michael-type reaction. In contrast, 6-substituted 7-azaindoles underwent regioselective C-3-alkylation through a Na[AuCl4]center dot 2H(2)O-catalyzed conjugate addition-type reaction. Analogously, the Na[AuCl4]center dot 2H(2)O-catalyzed reaction of 7-azaindole derivatives with beta-aryl-substituted alpha,beta-enones gave 3-substituted 7-azaindoles in moderate-to-satisfactory yields. Moreover, the Na [AuCl4]center dot 2H(2)O-catalyzed reaction of 1-substituted 7-azaindoles with alpha,beta-enones allowed an easy entry to 1,3-disubstituted 7-azaindoles in moderate-to-high yields. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
引用
收藏
页码:2393 / 2402
页数:10
相关论文
共 79 条
  • [11] DIAZAINDENES (AZAINDOLES) .6. PREPARATION AND SOME PROPERTIES OF 1,7-DIAZAINDENE 7-OXIDE AND 6,7,8,9-TETRAHYDRO-GAMMA-CARBOLINE 2-OXIDE
    CLARK, BAJ
    PARRICK, J
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (19): : 2270 - 2274
  • [12] C-HETEROARYLATION OF SUGARS BY INDOLYLBROMOMAGNESIUM SALTS - SYNTHESIS OF 3-(ALDITOL-1-YL)INDOLES AND THEIR CYCLIZATION TO INDOLE C-NUCLEOSIDE ANALOGS
    CORNIA, M
    CASIRAGHI, G
    ZETTA, L
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (18) : 5466 - 5468
  • [13] Carbolithiation of vinyl pyridines as a route to 7-azaindoles
    Cottineau, B
    O'Shea, DF
    [J]. TETRAHEDRON LETTERS, 2005, 46 (11) : 1935 - 1938
  • [14] COMPLEXES OF GOLD(III) WITH MONONEGATIVE BIDENTATE N,O-LIGANDS
    DAR, A
    MOSS, K
    COTTRILL, SM
    PARISH, RV
    MCAULIFFE, CA
    PRITCHARD, RG
    BEAGLEY, B
    SANDBANK, J
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1992, (12): : 1907 - 1913
  • [15] Unexpected formation of bis(1H-7-azaindol-3-yl)(2,4,5-trimethylphenyl)methane by erbium metal-induced C-H activation
    Deacon, GB
    Junk, PC
    Leary, SG
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (9-10) : 1115 - 1117
  • [16] A convenient one-pot synthesis of 4-, 6-, and 7-azaindoles from aminopyridines
    Debenham, SD
    Chan, A
    Liu, K
    Price, K
    Wood, HB
    [J]. TETRAHEDRON LETTERS, 2005, 46 (13) : 2283 - 2285
  • [17] Synthesis and benzodiazepine receptor (ω receptor) affinities of 3-substituted derivatives of pyrrolo [2,3-c]pyridine-5-carboxylate, a novel class of ω1 selective ligands
    Doisy, X
    Dekhane, M
    Le Hyaric, M
    Rousseau, JF
    Singh, SK
    Tan, S
    Guilleminot, V
    Schoemaker, H
    Sevrin, M
    George, P
    Potier, P
    Dodd, RH
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 1999, 7 (05) : 921 - 932
  • [18] Gold(III) chloride-catalyzed addition reactions of electron-rich arenes to methyl vinyl ketone
    Dyker, G
    Muth, E
    Hashmi, ASK
    Ding, L
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (11) : 1247 - 1252
  • [19] High yielding synthesis of heterocyclic β-substituted alanine derivatives
    Ferreira, PMT
    Maia, HLS
    Monteiro, LS
    [J]. TETRAHEDRON LETTERS, 1999, 40 (21) : 4099 - 4102
  • [20] Regioselective halogenation of 6-azaindoles: Efficient synthesis of 3-halo-2,3-disubstituted-6-azaindole derivatives
    Gallou, F
    Reeves, JT
    Tan, ZL
    Songa, JHJ
    Yee, NK
    Campbell, S
    Jones, PJ
    Senanayake, CH
    [J]. SYNLETT, 2005, (15) : 2400 - 2402