Intramolecular catalytic Friedel-Crafts reactions with allenyl cations for the synthesis of quinolines and their analogues

被引：64

作者：

Ishikawa, T

Manabe, S

Aikawa, T

Kudo, T

Saito, S ^{[1
]}

机构：

[1] Okayama Univ, Sch Engn, Dept Biosci & Biotechnol, Okayama 7008530, Japan

[2] Okayama Univ, Sch Educ, Okayama 7008530, Japan

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 14期

关键词：

D O I：

10.1021/ol049301u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This paper describes a novel method to synthesize a quinoline backbone by incorporating allenyl cations into a catalytic intramolecular Friedel-Crafts reaction. The initial products were isomerized and aromatized upon treatment with acid and base, respectively, to give quinolines. The basic concept also proved to be promising for 1-benzazepine, 1-benzazocine, or isoquinoline synthesis.

引用

收藏

页码：2361 / 2364

页数：4

相关论文

共 16 条

[1] THE STEREOCHEMISTRY OF ORGANOMETALLIC COMPOUNDS .35. HYDROFORMYLATION OF ORTHO-PROPENYLANILINES AND ORTHO-PROPENYLPHENOLS - A NEW ROUTE TO 4,5-DIHYDRO-3H-1-BENZAZEPINES [J].

ANASTASIOU, D ;

JACKSON, WR .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1992, 45 (01) :21-37

[2]

GILCHRUST TL, 1997, HETEROCYCLIC CHEM, P158

[3] Novel carbon-carbon bond-forming reactions using carbocations produced from substituted propargyl silyl ethers by the action of TMSOTf [J].

Ishikawa, T ;

Okano, M ;

Aikawa, T ;

Saito, S .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (13) :4635-4642

[4] [2+2]-CYCLOADDITIONS OF ALKENES WITH THE TRIPHENYLALLENYL CATION [J].

MAYR, H ;

BAUML, E .

TETRAHEDRON LETTERS, 1984, 25 (11) :1127-1130

[5] CONCERTED [4+2] AND STEPWISE [2+2] CYCLO-ADDITIONS OF THE TRIPHENYLALLENYL CATION WITH CYCLOPENTADIENE [J].

MAYR, H ;

BAUML, E .

TETRAHEDRON LETTERS, 1983, 24 (04) :357-360

[6] A mild and efficient one-step synthesis of quinolines [J].

McNaughton, BR ;

Miller, BL .

ORGANIC LETTERS, 2003, 5 (23) :4257-4259

[7] STEREOSPECIFIC AND STEREOSELECTIVE REACTIONS .1. PREPARATION OF AMINES FROM ALCOHOLS [J].

MITSUNOB.O ;

WADA, M ;

SANO, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (02) :679-&

[8] The (η6-benzene)Cr(CO)3-substituted propargyl cation:: Spectroscopic characterization and reactions of an ambident electrophile [J].

Muller, TJJ ;

Netz, AA .

ORGANOMETALLICS, 1998, 17 (16) :3609-3614

[9] CHEMISTRY AND SYNTHETIC UTILITY OF COBALT-COMPLEXED PROPARGYL CATIONS [J].

NICHOLAS, KM .

ACCOUNTS OF CHEMICAL RESEARCH, 1987, 20 (06) :207-214

[10] Ruthenium-catalyzed propargylation of aromatic compounds with propargylic alcohols [J].

Nishibayashi, Y ;

Yoshikawa, M ;

Inada, Y ;

Hidai, M ;

Uemura, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (40) :11846-11847