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 [J].
ALLEN, AD ;
CHIANG, Y ;
KRESGE, AJ ;
TIDWELL, TT .
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 [J].
ALLEN, MS ;
HAMAKER, LK ;
LALOGGIA, AJ ;
COOK, JM .
SYNTHETIC COMMUNICATIONS, 1992, 22 (14) :2077-2102
[4]   Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes [J].
Alonso, F ;
Beletskaya, IP ;
Yus, M .
CHEMICAL REVIEWS, 2004, 104 (06) :3079-3159
[5]   EVIDENCE OF THE FORMATION OF ZEROVALENT PALLADIUM FROM PD(OAC)2 AND TRIPHENYLPHOSPHINE [J].
AMATORE, C ;
JUTAND, A ;
MBARKI, MA .
ORGANOMETALLICS, 1992, 11 (09) :3009-3013
[6]   2,3-Disubstituted pyrrolo[2,3-b]quinoxalines via aminopalladation-reductive elimination [J].
Arcadi, A ;
Cacchi, S ;
Fabrizi, G ;
Parisi, LM .
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 [J].
ARCADI, A ;
CACCHI, S ;
CARNICELLI, V ;
MARINELLI, F .
TETRAHEDRON, 1994, 50 (02) :437-452
[8]   Pd-assisted multicomponent synthesis of heterocycles [J].
Balme, G ;
Bossharth, E ;
Monteiro, N .
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 [J].
Balme, G ;
Bouyssi, D ;
Lomberget, T ;
Monteiro, N .
SYNTHESIS-STUTTGART, 2003, (14) :2115-2134
[10]  
BALME G, 2002, HDB ORGANOPALLADIUM, V2, P2245