Sequential N-acylamide methylenation-enamide ring-closing metathesis:: a synthetic entry to 1,4-dihydroquinolines

被引：39

作者：

Bennasar, ML ^{[1
]}

Roca, T ^{[1
]}

Monerris, M ^{[1
]}

García-Díaz, D ^{[1
]}

机构：

[1] Univ Barcelona, Fac Pharm, Organ Chem Lab, E-08028 Barcelona, Spain

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 23期

关键词：

dimethyltitanocene; olefination; enamides; ring-closing metathesis; 1,4-dihydroquinolines;

D O I：

10.1016/j.tetlet.2005.04.028

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new synthetic entry to the 1,4-dihydroquinoline nucleus is reported. The procedure involves the dimethyltitanocene methylenation of N-(alkoxycarbonyl)amides derived from 2-allylanilines, followed by ring-closing metathesis of the resulting enamides. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：4035 / 4038

页数：4

共 38 条

[11] SYNTHESIS OF 2S,5S-AND 2R,5S-5-HYDROXYPIPECOLIC ACID VIA AMIDE-METHYLENATION OF S-5-HYDROXY-2-PIPERIDONE WITH DIMETHYLTITANOCENE
HERDEIS, C
HELLER, E
[J]. TETRAHEDRON-ASYMMETRY, 1993, 4 (09) : 2085 - 2094
[12] Studies towards the total synthesis of palau'amine. Formation of 4,5-dihydropyrrole-2-carboxylate intermediates by alkene-enamide ring-closing metathesis
Katz, JD
Overman, LE
[J]. TETRAHEDRON, 2004, 60 (43) : 9559 - 9568
[13] Enamide-olefin ring-closing metathesis
Kinderman, SS
van Maarseveen, JH
Schoemaker, HE
Hiemstra, H
Rutjes, FPJT
[J]. ORGANIC LETTERS, 2001, 3 (13) : 2045 - 2048
[14] Stereoselective formal synthesis of pseudodistomin C
Langlois, N
[J]. ORGANIC LETTERS, 2002, 4 (02) : 185 - 187
[15] Preparation of quinolines from resin-bound esters using titanium reagents
Macleod, C
Austin, CA
Hamprecht, DW
Hartley, RC
[J]. TETRAHEDRON LETTERS, 2004, 45 (48) : 8879 - 8882
[16] The first example of ring-closing olefin metathesis of dehydroamino acids: an application to the synthesis of azabicyclo[XY0]alkanes
Manzoni, L
Colombo, M
Scolastico, C
[J]. TETRAHEDRON LETTERS, 2004, 45 (12) : 2623 - 2625
[17] The reaction of dimethyltitanocene with N-substituted-β-lactams
Martínez, I
Howell, AR
[J]. TETRAHEDRON LETTERS, 2000, 41 (30) : 5607 - 5611
[18] Synthesis of substituted pyrrolidines and piperidines from endocyclic enamine derivatives.: Synthesis of (±)-laburnamine
Matos, MN
Afonso, CAM
Batey, RA
[J]. TETRAHEDRON, 2005, 61 (05) : 1221 - 1244
[19] Transition-metal-catalyzed reactions in heterocyclic synthesis
Nakamura, I
Yamamoto, Y
[J]. CHEMICAL REVIEWS, 2004, 104 (05) : 2127 - 2198
[20] A novel strategy for the solid-phase synthesis of substituted indolines
Nicolaou, KC
Roecker, AJ
Pfefferkorn, JA
Cao, GQ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (12) : 2966 - 2967

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