2-Alkylindoles via palladium-catalyzed reductive cyclization of ethyl 3-(o-trifluoroacetamidophenyl)-1-propargyl carbonates

被引:26
作者
Ambrogio, Ilaria [1 ]
Cacchi, Sandro [1 ]
Fabrizi, Giancarlo [1 ]
机构
[1] Univ Rome Studi La Sapienza, Dipartimento Chim & Tecnol Sostanze Biologicament, I-00185 Rome, Italy
关键词
alkylindoles; cyclization; palladium; alkynes; propargyl esters;
D O I
10.1016/j.tetlet.2007.07.213
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of ethyl 3-(o-trifluoroacetamidophenyl)-l-propargyl carbonates with formate anions in the presence of Pd(PPh3)4 affords 2-alkylindoles in good to excellent yields. (C) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7721 / 7725
页数:5
相关论文
共 37 条
[1]   Palladium-catalyzed synthesis of 2-(aminomethyl)indoles from ethyl 3-(o-trifluoroacetamidophenyl)-1-propargyl carbonate [J].
Ambrogio, I ;
Cacchi, S ;
Fabrizi, G .
ORGANIC LETTERS, 2006, 8 (10) :2083-2086
[2]   eta(3)-Propargyl/allenyl complexes of platinum and palladium of the type [(PPh(3))(2)M(eta(3)-CH(2)CCR)](+) [J].
Baize, MW ;
Blosser, PW ;
Plantevin, V ;
Schimpff, DG ;
Gallucci, JC ;
Wojcicki, A .
ORGANOMETALLICS, 1996, 15 (01) :164-173
[3]   Synthesis and functionalization of Indoles through palladium-catalyzed reactions [J].
Cacchi, S ;
Fabrizi, G .
CHEMICAL REVIEWS, 2005, 105 (07) :2873-2920
[4]   2,3-disubstituted indoles through the palladium-catalyzed reaction of aryl chlorides with o-alkynyltrifluoroacetanilides [J].
Cacchi, Sandro ;
Fabrizi, Giancarlo ;
Goggiamani, Antonella .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (10-11) :1301-1305
[5]   REACTIVITY OF ORGANOPHOSPHORUS COMPOUNDS .19. REDUCTION OF NITRO-COMPOUNDS BY TRIETHYL PHOSPHITE - A CONVENIENT NEW ROUTE TO CARBAZOLES INDOLES INDAZOLES TRIAZOLES AND RELATED COMPOUNDS [J].
CADOGAN, JIG ;
CAMERONW.M ;
MACKIE, RK ;
SEARLE, RJG .
JOURNAL OF THE CHEMICAL SOCIETY, 1965, (SEP) :4831-&
[6]   Highly regioselective synthesis of 2,3-disubstituted indenes via a novel palladium-catalyzed cyclization reaction of propargylic carbonates with carbon nucleophiles [J].
Duan, Xin-Hua ;
Guo, Li-Na ;
Bi, Hai-Peng ;
Liu, Xue-Yuan ;
Liang, Yong-Min .
ORGANIC LETTERS, 2006, 8 (25) :5777-5780
[7]  
FournierNguefack C, 1996, SYNLETT, P553
[8]  
GHARPURE M, 1991, SYNTHESIS-STUTTGART, P1079
[9]  
GOU LN, 2007, J ORG CHEM, V72, P1538
[10]   Practical methodologies for the synthesis of indoles [J].
Humphrey, Guy R. ;
Kuethe, Jeffrey T. .
CHEMICAL REVIEWS, 2006, 106 (07) :2875-2911