A simple two-step sequence for the synthesis of novel 4-aryl-4,5-dihydro-6H-[1,3]dioxolo[4,5-h]pyrrolo[1,2-a][1]benzazepin-6-ones from 6-amino-3,4-methylenedioxyacetophenone

被引：13

作者：

Abonia, Rodrigo ^{[1
]}

Cuervo, Paola ^{[1
]}

Insuasty, Braulio ^{[1
]}

Quiroga, Jairo ^{[1
]}

Nogueras, Manuel ^{[2
]}

Cobo, Justo ^{[2
]}

机构：

[1] Univ Valle, Dept Quim, Cali 25360, Colombia

[2] Univ Jaen, Dept Quim Inorgan & Organ, Jaen 23071, Spain

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 2008卷 / 27期

关键词：

phosphoric acid; Michael addition; chalcones; cyclization; heterocycles;

D O I：

10.1002/ejoc.200800493

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein is provided an efficient and two-step short procedure for the synthesis of novel 6H-[1,3]dioxolobenzo[4,5-h]pyrrolo[1,2-a][1]benezazepin-6-one derivatives promoted by commercial phosphoric acid. In a parallel approach some pyrrolyl chalcones were isolated that proved to behave as intermediates for the title compounds. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).

引用

收藏

页码：4684 / 4689

页数：6

相关论文

共 27 条

[1] A versatile synthesis of 4,5-dihydropyrrolo[1,2-a]quinoxalines [J].

Abonia, R ;

Insuasty, B ;

Quiroga, J ;

Kolshorn, H ;

Meier, H .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2001, 38 (03) :671-674

[2]

ABONIA R, 2008, OPEN ORG CHEM J, V2, P26

[3] The influence of chiral auxiliaries and catalysts on the selectivity of intramolecular conjugate additions of pyrrole to N-tethered Michael acceptors [J].

Banwell, MG ;

Beck, DAS ;

Smith, JA .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (02) :157-159

[4] Characterization of H+-ATPase-dependent activity of multi drug resistance-associated protein in homoharringtonine-resistant human leukemic K562 cells [J].

Benderra, Z ;

Morjani, H ;

Trussardi, A ;

Manfait, M .

LEUKEMIA, 1998, 12 (10) :1539-1544

[5] Synthesis. of new molecular probes for investigation of steroid biosynthesis induced by selective interaction with peripheral type benzodiazepine receptors (PBR) [J].

Campiani, G ;

Ramunno, A ;

Fiorini, I ;

Nacci, V ;

Morelli, E ;

Novellino, E ;

Goegan, M ;

Mennini, T ;

Sullivan, S ;

Zisterer, DM ;

Williams, CD .

JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (19) :4276-4281

[6] FURTHER CYCLISATION REACTIONS OF 1-ARYLPYRROLES [J].

CHEESEMAN, GW ;

RAFIQ, M .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (15) :2732-+

[7] 1-(6-amino-1,3-benzodioxol-5-yl)-3-(4-pyridyl)prop-2-en-1-one crystallizes with Z′=2:: hydrogen-bonded supra-molecular substructures in one and two dimensions, each containing only one type of molecule [J].

Cuervo, Paola ;

Abonia, Rodrigo ;

Cobo, Justo ;

Low, John N. ;

Glidewell, Christopher .

ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2007, 63 :O99-O101

[8] A simple, efficient access to functionalized pyrrolobenzazepines related to the ABC core of cephalotaxine [J].

deOliveira, ER ;

Dumas, F ;

dAngelo, J .

TETRAHEDRON LETTERS, 1997, 38 (21) :3723-3726

[9] The importance of complex stability for asymmetric copper-catalyzed cyclopropanations in [emim][OTf] ionic liquid:: the bis(oxazoline)-azabis(oxazoline) case [J].

Fraile, JM ;

García, JI ;

Herrerías, CI ;

Mayoral, JA ;

Reiser, O ;

Vaultier, M .

TETRAHEDRON LETTERS, 2004, 45 (36) :6765-6768

[10] Analogs of 3-hydroxy-1H-1-benzazepine-2,5-dione: Structure-activity relationship at N-methyl-D-aspartate receptor glycine sites [J].

Guzikowski, AP ;

Cai, SX ;

Espitia, SA ;

Hawkinson, JE ;

Huettner, JE ;

Nogales, DF ;

Tran, M ;

Woodward, RM ;

Weber, E ;

Keana, JFW .

JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (23) :4643-4653