Microwave-assisted multi-step synthesis of novel pyrrolo-[3,2-c]quinoline derivatives

被引：38

作者：

Benakki, Hafid ^{[1
,2
,3
]}

Colacino, Evelina ^{[1
,2
]}

Andre, Christophe ^{[1
,2
]}

Guenoun, Farhate ^{[3
]}

Martinez, Jean ^{[1
,2
]}

Lamaty, Frederic ^{[1
,2
]}

机构：

[1] Univ Montpellier I, Inst Biomol Max Mousseron, CNRS, UMR 5247, F-34095 Montpellier 05, France

[2] Univ Montpellier 2, F-34095 Montpellier 05, France

[3] Univ My Ismail, Fac Sci, Zitoune, Meknes, Morocco

来源：

TETRAHEDRON | 2008年 / 64卷 / 25期

关键词：

microwave activation; Suzuki coupling; Aza-Baylis-Hillman; ring-closing metathesis;

D O I：

10.1016/j.tet.2008.04.034

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new approach for the synthesis of original substituted pyrrolo-[3,2-c]quinoline derivatives using microwave-assisted chemistry is described. The use of microwave activation in this synthesis resulted in high yielding and clean steps. The key step for introducing diversity is the amination or the Pd-catalyzed cross-coupling of an imidoyl chloride derivative, obtained in a straightforward manner and in good yield. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：5949 / 5955

页数：7

共 53 条

[1] Chiral quinuclidine-based amine catalysts for the asymmetric one-pot, three-component aza-Baylis-Hillman reaction [J].

Balan, D ;

Adolfsson, H .

TETRAHEDRON LETTERS, 2003, 44 (12) :2521-2524

[2] Titanium isopropoxide as efficient catalyst for the aza-Baylis-Hillman reaction.: Selective formation of α-methylene-β-amino acid derivatives [J].

Balan, D ;

Adolfsson, H .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (07) :2329-2334

[3] Selective formation of α-methylene-β-amino acid derivatives through the aza version of the Baylis-Hillman reaction [J].

Balan, D ;

Adolfsson, H .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (19) :6498-6501

[4] PHOSPHINE MEDIATED SYNTHESIS OF 2-METHYLIDENE-3-AMINO ESTERS AND KETONES [J].

BERTENSHAW, S ;

KAHN, M .

TETRAHEDRON LETTERS, 1989, 30 (21) :2731-2732

[5] Advanced fine-tuning of Grubbs/Hoveyda olefin metathesis catalysts: a further step toward an optimum balance between antinomic properties [J].

Bieniek, Michal ;

Bujok, Robert ;

Cabaj, Maciej ;

Lugan, Noel ;

Lavigne, Guy ;

Arlt, Dieter ;

Grela, Karol .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (42) :13652-13653

[6] REVERSIBLE INHIBITORS OF THE GASTRIC (H+/K+)-ATPASE .1. 1-ARYL-4-METHYLPYRROLO[3,2-C]QUINOLINES AS CONFORMATIONALLY RESTRAINED ANALOGS OF 4-(ARYLAMINO)QUINOLINES [J].

BROWN, TH ;

IFE, RJ ;

KEELING, DJ ;

LAING, SM ;

LEACH, CA ;

PARSONS, ME ;

PRICE, CA ;

REAVILL, DR ;

WIGGALL, KJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (02) :527-533

[7] Pyrroloquinoxaline derivatives as high-affinity and selective 5-HT3 receptor agonists:: Synthesis, further structure-activity relationships, and biological studies [J].

Campiani, G ;

Morelli, E ;

Gemma, S ;

Nacci, V ;

Butini, S ;

Hamon, M ;

Novellino, E ;

Greco, G ;

Cagnotto, A ;

Goegan, M ;

Cervo, L ;

Dalla Valle, F ;

Fracasso, C ;

Caccia, S ;

Mennini, T .

JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (21) :4362-4379

[8] Novel and highly potent 5-HT3 receptor agonists based on a pyrroloquinoxaline structure [J].

Campiani, G ;

Cappelli, A ;

Nacci, V ;

Anzini, M ;

Vomero, S ;

Hamon, M ;

Cagnotto, A ;

Fracasso, C ;

Uboldi, C ;

Caccia, S ;

Consolo, S ;

Mennini, T .

JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (22) :3670-3678

[9] Novel potent and selective central 5-HT3 receptor ligands provided with different intrinsic efficacy.: 2.: Molecular basis of the intrinsic efficacy of arylpiperazine derivatives at the central 5-HT3 receptors [J].

Cappelli, A ;

Anzini, M ;

Vomero, S ;

Canullo, L ;

Mennuni, L ;

Makovec, F ;

Doucet, E ;

Hamon, M ;

Menziani, MC ;

De Benedetti, PG ;

Bruni, G ;

Romeo, MR ;

Giorgi, G ;

Donati, A .

JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (09) :1556-1575

[10] Carbon-carbon bond-forming reductive elimination from arylpalladium complexes containing functionalized alkyl groups. Influence of ligand steric and electronic properties on structure, stability, and reactivity [J].

Culkin, DA ;

Hartwig, JF .

ORGANOMETALLICS, 2004, 23 (14) :3398-3416

← 1 2 3 4 5 6 →