Palladium-catalyzed reaction of o-alkynyltrifluoroacetanilides with 1-bromoalkynes.: An approach to 2-substituted 3-alkynylindoles and 2-substituted 3-acylindoles

被引:91
作者
Arcadi, A
Cacchi, S
Fabrizi, G
Marinelli, F
Parisi, LM
机构
[1] Univ Roma La Sapienza, Dipartimento Studi Chim & Tecnol Sostanze Biologi, I-00185 Rome, Italy
[2] Univ Aquila, Dipartimento Chim Ingn Chim & Mat, Fac Sci, I-67100 Laquila, Italy
关键词
D O I
10.1021/jo050517z
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The palladium-catalyzed reaction of o-alkynyltrifluoroacetanilides with 1-bromoalkynes affords free N-H 2-substituted 3-alkynylindoles in satisfactory to high yield. 2-Substituted 3-alkynylindoles revealed useful intermediates for the regioselective synthesis of 2-substituted 3-acylindoles. The latter can be prepared from o-alkynyltrifluoroacetanilides and 1-bromoalkynes via a one-pot cyclization-hydration protocol, omitting the isolation of 2-substituted 3-alkynylindoles.
引用
收藏
页码:6213 / 6217
页数:5
相关论文
共 52 条
  • [1] Abbiati G, 2001, SYNTHESIS-STUTTGART, P2477
  • [2] SUBSTITUENT EFFECTS ON THE ACID HYDRATION OF ACETYLENES
    ALLEN, AD
    CHIANG, Y
    KRESGE, AJ
    TIDWELL, TT
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (05) : 775 - 779
  • [3] ENTRY INTO 6-METHOXY-D(+)-TRYPTOPHANS - STEREOSPECIFIC SYNTHESIS OF 1-BENZENESULFONYL-6-METHOXY-D(+)-TRYPTOPHAN ETHYL-ESTER
    ALLEN, MS
    HAMAKER, LK
    LALOGGIA, AJ
    COOK, JM
    [J]. SYNTHETIC COMMUNICATIONS, 1992, 22 (14) : 2077 - 2102
  • [4] Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes
    Alonso, F
    Beletskaya, IP
    Yus, M
    [J]. CHEMICAL REVIEWS, 2004, 104 (06) : 3079 - 3159
  • [5] EVIDENCE OF THE FORMATION OF ZEROVALENT PALLADIUM FROM PD(OAC)2 AND TRIPHENYLPHOSPHINE
    AMATORE, C
    JUTAND, A
    MBARKI, MA
    [J]. ORGANOMETALLICS, 1992, 11 (09) : 3009 - 3013
  • [6] 2,3-Disubstituted pyrrolo[2,3-b]quinoxalines via aminopalladation-reductive elimination
    Arcadi, A
    Cacchi, S
    Fabrizi, G
    Parisi, LM
    [J]. TETRAHEDRON LETTERS, 2004, 45 (11) : 2431 - 2434
  • [7] 2-SUBSTITUTED-3-ACYLINDOLES THROUGH THE PALLADIUM-CATALYZED CARBONYLATIVE CYCLIZATION OF 2-ALKYNYLTRIFLUOROACETANILIDES WITH ARYL HALIDES AND VINYL TRIFLATES
    ARCADI, A
    CACCHI, S
    CARNICELLI, V
    MARINELLI, F
    [J]. TETRAHEDRON, 1994, 50 (02) : 437 - 452
  • [8] Pd-assisted multicomponent synthesis of heterocycles
    Balme, G
    Bossharth, E
    Monteiro, N
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (21) : 4101 - 4111
  • [9] Cyclisations involving attack of carbo- and heteronucleophiles on carbon-carbon π-bonds activated by organopalladium complexes
    Balme, G
    Bouyssi, D
    Lomberget, T
    Monteiro, N
    [J]. SYNTHESIS-STUTTGART, 2003, (14): : 2115 - 2134
  • [10] BALME G, 2002, HDB ORGANOPALLADIUM, V2, P2245