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 [J].

HERDEIS, C ;

HELLER, E .

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 [J].

Katz, JD ;

Overman, LE .

TETRAHEDRON, 2004, 60 (43) :9559-9568

[13] Enamide-olefin ring-closing metathesis [J].

Kinderman, SS ;

van Maarseveen, JH ;

Schoemaker, HE ;

Hiemstra, H ;

Rutjes, FPJT .

ORGANIC LETTERS, 2001, 3 (13) :2045-2048

[14] Stereoselective formal synthesis of pseudodistomin C [J].

Langlois, N .

ORGANIC LETTERS, 2002, 4 (02) :185-187

[15] Preparation of quinolines from resin-bound esters using titanium reagents [J].

Macleod, C ;

Austin, CA ;

Hamprecht, DW ;

Hartley, RC .

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 [J].

Manzoni, L ;

Colombo, M ;

Scolastico, C .

TETRAHEDRON LETTERS, 2004, 45 (12) :2623-2625

[17] The reaction of dimethyltitanocene with N-substituted-β-lactams [J].

Martínez, I ;

Howell, AR .

TETRAHEDRON LETTERS, 2000, 41 (30) :5607-5611

[18] Synthesis of substituted pyrrolidines and piperidines from endocyclic enamine derivatives.: Synthesis of (±)-laburnamine [J].

Matos, MN ;

Afonso, CAM ;

Batey, RA .

TETRAHEDRON, 2005, 61 (05) :1221-1244

[19] Transition-metal-catalyzed reactions in heterocyclic synthesis [J].

Nakamura, I ;

Yamamoto, Y .

CHEMICAL REVIEWS, 2004, 104 (05) :2127-2198

[20] A novel strategy for the solid-phase synthesis of substituted indolines [J].

Nicolaou, KC ;

Roecker, AJ ;

Pfefferkorn, JA ;

Cao, GQ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (12) :2966-2967

← 1 2 3 4 →