An efficient and simple aminobenzannulation reaction: Pyrrolidine as a trigger for the synthesis of 1-amino-acridines

被引：47

作者：

Belmont, P ^{[1
]}

Belhadj, T ^{[1
]}

机构：

[1] Univ Lyon 1, CNRS, UMR 5181, F-69622 Villeurbanne, France

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 09期

关键词：

D O I：

10.1021/ol050380z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new aminobenzannulation methodology has been developed and applied successfully to the synthesis of 1-amino-acridines. The key and last step goes through an enamine intermediate that was detected in some cases. When pyrrolidine and powdered 4 angstrom molecular sieves were used, the enamine synthesis and the aminobenzannulation step took place subsequently, whereas for other secondary amines, neutral Al2O3 or PtCl2 catalysis was necessary.

引用

页码：1793 / 1795

页数：3

共 29 条

[1]

ALBERT A, 1952, HETEROCYCL COMPOUNDS, P4

[2]

[Anonymous], 1966, EDWARD ARNOLD

[3] Reorganization of enynes catalyzed by platinum salts [J].

Añorbe, L ;

Domínguez, G ;

Pérez-Castells, J .

CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (20) :4938-4943

[4] POTENTIAL ANTITUMOR AGENTS .50. INVIVO SOLID-TUMOR ACTIVITY OF DERIVATIVES OF N-[2-(DIMETHYLAMINO)ETHYL]ACRIDINE-4-CARBOXAMIDE [J].

ATWELL, GJ ;

REWCASTLE, GW ;

BAGULEY, BC ;

DENNY, WA .

JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (04) :664-669

[5] The behavior of 1,n-enynes in the presence of transition metals [J].

Aubert, C ;

Buisine, O ;

Malacria, M .

CHEMICAL REVIEWS, 2002, 102 (03) :813-834

[6] Regioselective synthesis of substituted naphthalenes:: A novel de novo approach based on a metal-free protocol for stepwise cycloaddition of o-alkynylbenzaldehyde derivatives with either alkynes or alkenes [J].

Barluenga, J ;

Váquez-Villa, H ;

Ballesteros, A ;

González, JM .

ORGANIC LETTERS, 2003, 5 (22) :4121-4123

[7] New methodology for acridine synthesis using a rhodium-catalyzed benzannulation [J].

Belmont, P ;

Andrez, JC ;

Allan, CSM .

TETRAHEDRON LETTERS, 2004, 45 (13) :2783-2786

[8]

Bernthsen A., 1883, CHEM BER, V16, P1802

[9] Heterodimeric tacrine-based acetylcholinesterase inhibitors: Investigating ligand-peripheral site interactions [J].

Carlier, PR ;

Chow, ESH ;

Han, YF ;

Liu, J ;

El Yazal, J ;

Pang, YP .

JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (20) :4225-4231

[10] IMPROVED TITANIUM TETRACHLORIDE PROCEDURE FOR ENAMINE SYNTHESIS .2. SCOPE OF THE REACTION [J].

CARLSON, R ;

NILSSON, A .

ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1984, 38 (01) :49-53

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