Synthesis of five-, six-, and seven-membered ring lactams by Cp*Rh complex-catalyzed oxidative N-heterocyclization of amino alcohols

被引:197
作者
Fujita, K [1 ]
Takahashi, Y [1 ]
Owaki, M [1 ]
Yamamoto, K [1 ]
Yamaguchi, R [1 ]
机构
[1] Kyoto Univ, Grad Sch Human & Environm Studies, Kyoto 6068501, Japan
关键词
D O I
10.1021/ol0489954
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new effective catalytic system consisting of [Cp*RhCl2](2)/K2CO3 (CP* = pentamethylcyclopentadienyl) for the lactamization of amino alcohols has been developed. As an example, the reaction of 3-(2-aminophenyl)-1-propanol in the presence of [Cp*RhCl2](2) (5.0% Rh) and K2CO3 (10%) in acetone gives 3,4-dihydro-2(1h)-quinolinone in an isolated yield of 80%. A variety of five-, six-, and seven-membered benzo-fused lactams are synthesized by this catalytic system.
引用
收藏
页码:2785 / 2788
页数:4
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共 35 条
[1]  
[Anonymous], J AM CHEM SOC
[2]   Catalytic asymmetric synthesis of quaternary carbon centers.: Exploratory studies of intramolecular Heck reactions of (Z)-α,β-unsaturated anilides and mechanistic investigations of asymmetric Heck reactions proceeding via neutral intermediates [J].
Ashimori, A ;
Bachand, B ;
Calter, MA ;
Govek, SP ;
Overman, LE ;
Poon, DJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (26) :6488-6499
[3]   Catalytic asymmetric synthesis of quaternary carbon centers.: Exploratory investigations of intramolecular Heck reactions of (E)-α,β-Unsaturated 2-haloanilides and analogues to form enantioenriched spirocyclic products [J].
Ashimori, A ;
Bachand, B ;
Overman, LE ;
Poon, DJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (26) :6477-6487
[4]   SUBSTITUTED OXINDOLES .I. PREPARATION AND SPECTRAL CHARACTERISTICS OF SOME SIMPLE OXINDOLE DERIVATIVES [J].
BECKETT, AH ;
DAISLEY, RW ;
WALKER, J .
TETRAHEDRON, 1968, 24 (19) :6093-&
[5]   SYNTHESIS OF OXINDOLES BY RADICAL CYCLIZATION [J].
BOWMAN, WR ;
HEANEY, H ;
JORDAN, BM .
TETRAHEDRON LETTERS, 1988, 29 (50) :6657-6660
[6]   LIGAND EFFECTS IN THE RHODIUM(II)-CATALYZED REACTIONS OF ALPHA-DIAZOAMIDES - OXINDOLE FORMATION IS PROMOTED BY THE USE OF RHODIUM(II) PERFLUOROCARBOXAMIDE CATALYSTS [J].
BROWN, DS ;
ELLIOTT, MC ;
MOODY, CJ ;
MOWLEM, TJ ;
MARINO, JP ;
PADWA, A .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (09) :2447-2455
[7]   Palladium-catalyzed α-arylation of carbonyl compounds and nitriles [J].
Culkin, DA ;
Hartwig, JF .
ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (04) :234-245
[8]   RHODIUM(II) ACETATE AND NAFION-H CATALYZED DECOMPOSITION OF N-ARYLDIAZOAMIDES - AN EFFICIENT SYNTHESIS OF 2(3H)-INDOLINONES [J].
DOYLE, MP ;
SHANKLIN, MS ;
PHO, HQ ;
MAHAPATRO, SN .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (05) :1017-1022
[9]   Regio- and chemoselective transfer hydrogenation of quinolines catalyzed by a Cp*Ir complex [J].
Fujita, K ;
Kitatsuji, C ;
Furukawa, S ;
Yamaguchi, R .
TETRAHEDRON LETTERS, 2004, 45 (16) :3215-3217
[10]   N-Alkylation of amines with alcohols catalyzed by a Cp*Ir complex [J].
Fujita, K ;
Li, ZZ ;
Ozeki, N ;
Yamaguchi, R .
TETRAHEDRON LETTERS, 2003, 44 (13) :2687-2690