Synthesis of substituted 1,2-dihydroquinolines and quinolines using ene-ene metathesis and ene-enol ether metathesis

被引：111

作者：

Arisawa, M ^{[1
]}

Theeraladanon, C ^{[1
]}

Nishida, A ^{[1
]}

Nakagawa, M ^{[1
]}

机构：

[1] Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 45期

关键词：

1,2-dihydroquinoline; quinoline; quinoline alkaloid; ring-closing metathesis; ene-ene metathesis; enol silyl ether-ene metathesis; ene-enol ether metathesis;

D O I：

10.1016/S0040-4039(01)01714-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We describe a novel and convenient method for quinoline synthesis using ring-closing olefin metathesis (RCM), ene-ene metathesis, and ene-enol ether metathesis. We also report the first example of enol silyl ether-ene metathesis to produce cyclic enol silyl ether. Using this method, versatile substituted quinoline derivatives were readily prepared in excellent yield from anthranilic acid derivatives. C 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：8029 / 8033

页数：5

共 16 条

[1]

AINIER JD, 2001, TETRAHEDRON LETT, V42, P179

[2]

Arisawa M, 1997, SYNLETT, P1179

[3]

Arisawa M, 2000, CHEM PHARM BULL, V48, P1593

[4] Concise synthesis of azacycloundecenes using ring-closing metathesis (RCM) [J].

Arisawa, M ;

Kato, C ;

Kaneko, H ;

Nishida, A ;

Nakagawa, M .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (12) :1873-1876

[5]

Arisawa M, 2000, SYNLETT, P841

[6]

Clark JS, 1999, TETRAHEDRON, V55, P8231

[7] A new route to C-glycosylidene compounds mediated by olefin metathesis [J].

Dirat, O ;

Vidal, T ;

Langlois, Y .

TETRAHEDRON LETTERS, 1999, 40 (26) :4801-4802

[8]

Fürstner A, 2000, ANGEW CHEM INT EDIT, V39, P3012

[9]

Jones G., 1996, Elsevier, V5, P167

[10] New approaches to total synthesis of manzamine A, ircinal A and related compounds [J].

Nakagawa, M ;

Torisawa, Y ;

Uchida, H ;

Nishida, A .

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1999, 57 (11) :1004-1015

← 1 2 →