A general strategy for the synthesis of oxoisoindolo[2,1-a]quinoline derivatives:: the first efficient synthesis of 5,6,6a,11-tetrahydro-11-oxoisoindolo[2,1-a]-quinoline-10-carboxylic acids

被引：25

作者：

Varlamov, AV ^{[1
]}

Zubkov, FI ^{[1
]}

Boltukhina, EV ^{[1
]}

Sidorenko, NV ^{[1
]}

Borisov, RS ^{[1
]}

机构：

[1] Patrice Lumumba Peoples Friendship Univ, Dept Organ Chem, Moscow 117198, Russia

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 18期

基金：

俄罗斯基础研究基金会;

关键词：

intramolecular Diels-Alder reaction; isoindoloquinoline; homoallylamine;

D O I：

10.1016/S0040-4039(03)00705-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient two-step synthesis of new isoindolo[2,1-a]quinoline-10-carboxylic acids via [4+2] cycloaddition of the 4-alpha-furyl-4-N-arylaminobut-1-enes and maleic anhydride is described. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：3641 / 3643

页数：3

共 10 条

[1] Study on the benzoyl derivatives of indigo VII [J].

de Diesbach, H ;

Rey-Bellet, G ;

Kiang, TS .

HELVETICA CHIMICA ACTA, 1943, 26 :1869-1885

[2] Application of organolithium and related reagents in synthesis.: Part 23:: Synthetic strategies based on ortho-aromatic metallation.: Synthesis of 4b-arylisoindolo[2,1-a]quinoline derivatives [J].

Epsztajn, J ;

Józwiak, A ;

Koluda, P ;

Sadokierska, I ;

Wilkowska, ID .

TETRAHEDRON, 2000, 56 (27) :4837-4844

[3] SYNTHESIS OF ISOINDOLO[2,1-A]QUINOLINE DERIVATIVES AND THEIR EFFECTS ON N2-INDUCED HYPOXIA [J].

ISHIHARA, Y ;

KIYOTA, Y ;

GOTO, G .

CHEMICAL & PHARMACEUTICAL BULLETIN, 1990, 38 (11) :3024-3030

[4] Some aspects of reduced quinoline chemistry [J].

Kouznetsov, V ;

Palma, A ;

Ewert, C ;

Varlamov, A .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1998, 35 (04) :761-785

[5] Acyliminium ion-olefin cyclization leading to isoindolo [2,1-a]quinoline derivatives [J].

Pigeon, P ;

Othman, M ;

Netchitaïlo, P ;

Decroix, B .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1999, 36 (03) :691-695

[6] Novel approach to isoindolo[2,1-a]quinolines [J].

Pigeon, P ;

Decroix, B .

SYNTHETIC COMMUNICATIONS, 1998, 28 (13) :2507-2516

[7]

PUENTES CO, 2002, J HETEROCYCLIC CHEM, V39, P1

[8]

SUGASAWA S, 1942, J PHARM SOC JPN, V62, P367

[9] Synthesis and inhibitory activity of novel tri- and tetracyclic quinolines against topoisomerases [J].

Sui, ZH ;

Altom, J ;

Nguyen, V ;

Fernandez, J ;

Bernstein, JI ;

Hiliard, JJ ;

Barrett, JF ;

Podlogar, BL ;

Ohemeng, KA .

BIOORGANIC & MEDICINAL CHEMISTRY, 1998, 6 (06) :735-742

[10]

Varlamov A, 2002, SYNTHESIS-STUTTGART, P771

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