Synthesis of tricyclic quinolones and naphthyridones by intramolecular heck cyclization of functionalized electron-rich heterocycles

被引：51

作者：

Beccalli, EM

Broggini, G

Martinelli, M

Paladino, G

Zoni, C

机构：

[1] Univ Milan, Fac Farm, Ist Chim Organ A Marchesini, I-20133 Milan, Italy

[2] Univ Insubria, Dipartimento Sci Chem & Ambientali, I-22100 Como, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 2005卷 / 10期

关键词：

heck reaction; palladium; cyclization; lactam; microwaves;

D O I：

10.1002/ejoc.200400817

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Starting from commercially available pyrrole- and thiophene-2-carboxylic acids 1 or thiophene- and furan-3-carboxylic acids 6, we report the synthesis of tricyclic fused quinolone and naphthyridone derivatives, in only three steps, by an intramolecular Heck cyclization. We also report the use of microwave irradiation to obtain, in some cases, better yields of cyclized products. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

引用

收藏

页码：2091 / 2096

页数：6

相关论文

共 44 条

[1] Regioselectivity on the palladium-catalyzed intramolecular cyclization of indole derivatives [J].

Abbiati, G ;

Beccalli, EM ;

Broggini, G ;

Zoni, C .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (20) :7625-7628

[2]

Alazard JP, 1996, B SOC CHIM FR, V133, P251

[3] Palladium-mediated approach to dibenzo[b,e][1,4]diazepines and benzopyrido-analogues.: An efficient synthesis of tarpane [J].

Beccalli, EM ;

Broggini, G ;

Paladino, G ;

Zoni, C .

TETRAHEDRON, 2005, 61 (01) :61-68

[4] Uncommon intramolecular palladium-catalyzed cyclization of indole derivatives [J].

Beccalli, EM ;

Broggini, G .

TETRAHEDRON LETTERS, 2003, 44 (09) :1919-1921

[5] Intramolecular Heck reaction of 2- and 3-iodoindole derivatives for the synthesis of β- and γ-carbolinones [J].

Beccalli, EM ;

Broggini, G ;

Marchesini, A ;

Rossi, E .

TETRAHEDRON, 2002, 58 (33) :6673-6678

[6] The heck reaction as a sharpening stone of palladium catalysis [J].

Beletskaya, IP ;

Cheprakov, AV .

CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066

[7]

BLYTHIN DJ, 1984, Patent No. 127135

[8]

BLYTHIN DJ, 1988, Patent No. 4740511

[9] Synthesis and cytotoxic activity of N-[2-(dimethylamino)ethyl] carboxamide derivatives of benzofuro[2,3-b]quinoline, 6H-quinindoline, indeno[2,1-b] quinoline and [1] benzothieno[2,3-b] quinoline [J].

Bu, XY ;

Deady, LW ;

Denny, WA .

AUSTRALIAN JOURNAL OF CHEMISTRY, 2000, 53 (02) :143-147

[10] Synthesis and cytotoxic activity evaluation of indolo-, pyrrolo-, and benzofuro-quinolin-2(1H)-ones and 6-anilinoindoloquinoline derivatives [J].

Chen, YL ;

Chung, CH ;

Chen, IL ;

Chen, PH ;

Jeng, HY .

BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (08) :2705-2712

← 1 2 3 4 5 →