Synthesis of benzannulated N-heterocycles by a palladium-catalyzed C-C/C-N coupling of bromoalkylamines

被引:92
作者
Thansandote, Praew [1 ]
Raemy, Manuel [1 ]
Rudolph, Alena [1 ]
Lautens, Mark [1 ]
机构
[1] Univ Toronto, Dept Chem, Davenport Res Labs, Toronto, ON M5S 3H6, Canada
关键词
D O I
10.1021/ol702472u
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A palladium-catalyzed domino intermolecular alkylation/intramolecular amination of functionalized aryl iodides represents a new strategy for the synthesis of benzannulated N-heterocycles, affording functionalized indolines and tetrahydroquinolines from simple precursors.
引用
收藏
页码:5255 / 5258
页数:4
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共 41 条
[1]   Pharmacological characteristics of indoline derivatives in muscarinic receptor subtypes [J].
Adachi, S ;
Koike, K ;
Takayanagi, I .
PHARMACOLOGY, 1996, 53 (04) :250-258
[2]   The selective reaction of aryl halides with KOH: Synthesis of phenols, aromatic ethers, and benzofurans [J].
Anderson, Kevin W. ;
Ikawa, Takashi ;
Tundel, Rachel E. ;
Buchwald, Stephen L. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (33) :10694-10695
[3]   Titanocene-based method for indole synthesis [J].
Aoki, K ;
Peat, AJ ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (13) :3068-3073
[4]   Preparation of differentially 1,3-disubstituted indolines by intramolecular carbolithiation [J].
Bailey, WF ;
Luderer, MR ;
Mealy, MJ .
TETRAHEDRON LETTERS, 2003, 44 (28) :5303-5305
[5]   Synthesis of 2,3-dihydroindoles, indoles, and anilines by transition metal-free amination of aryl chlorides [J].
Beller, M ;
Breindl, C ;
Riermeier, TH ;
Tillack, A .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (04) :1403-1412
[6]   5-HYDROXYTRYPTAMINE (5-HT3) RECEPTOR ANTAGONISTS .2. 1-INDOLINECARBOXAMIDES [J].
BERMUDEZ, J ;
DABBS, S ;
JOINER, KA ;
KING, FD .
JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (07) :1929-1932
[7]   A route to annulated indoles via a palladium-catalyzed tandem alkylation/direct arylation reaction [J].
Bressy, C ;
Alberico, D ;
Lautens, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (38) :13148-13149
[8]   A catalytic process based on sequential ortho-alkylation and vinylation of ortho-alkylaryl iodides via palladacycles [J].
Catellani, M ;
Cugini, F .
TETRAHEDRON, 1999, 55 (21) :6595-6602
[9]   A metal-free approach to the synthesis of indoline derivatives by a phenyliodine(III) bis(trifluoroacetate)-mediated amidohydroxylation reaction [J].
Correa, Arkaitz ;
Tellitu, Imanol ;
Dominguez, Esther ;
SanMartin, Raul .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (21) :8316-8319
[10]   Synthesis of highly substituted indolines and indoles via intramolecular [4+2] cycloaddition of ynamides and conjugated enynes [J].
Dunetz, JR ;
Danheiser, RL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (16) :5776-5777