Catalyst-free microwave-assisted amination of 2-chloro-5-nitrobenzoic acid

被引：24

作者：

Baqi, Younis ^{[1
]}

Mueller, Christa E. ^{[1
]}

机构：

[1] Univ Bonn, D-53121 Bonn, Germany

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 15期

关键词：

D O I：

10.1021/jo070731i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of N-substituted 5-nitroanthranilic acid derivatives 3a-w was achieved by a new, mild, microwave-assisted, regioselective amination reaction of 5-nitro-2-chlorobenzoic acid (1a) with a diverse range of aliphatic and aromatic amines 2a-w without added solvent or catalyst. Up to > 99% isolated yield was obtained within 5-30 min at 80-120 degrees C. The reaction, which is suitable for upscaling, yielded new compounds that are of considerable interest as useful building blocks and as potential drugs.

引用

收藏

页码：5908 / 5911

页数：4

相关论文

共 47 条

[1] Rapid and efficient microwave-assisted copper(0)-catalyzed ullmann coupling reaction:: General access to anilinoanthraquinone derivatives [J].

Baqi, Younis ;

Mueller, Christa E. .

ORGANIC LETTERS, 2007, 9 (07) :1271-1274

[2] Development of nonsteroidal anti-inflammatory drug analogs and steroid carboxylates selective for human aldo-keto reductase isoforms: Potential antineoplastic agents that work independently of cyclooxygenase isozymes [J].

Bauman, DR ;

Rudnick, SI ;

Szewczuk, LM ;

Jin, Y ;

Gopishetty, S ;

Penning, TM .

MOLECULAR PHARMACOLOGY, 2005, 67 (01) :60-68

[3] Synthesis and evaluation of inhibitors of transthyretin amyloid formation based on the non-steroidal anti-inflammatory drug, flufenamic acid [J].

Baures, PW ;

Oza, VB ;

Peterson, SA ;

Kelly, JW .

BIOORGANIC & MEDICINAL CHEMISTRY, 1999, 7 (07) :1339-1347

[4] Intercalators as anticancer drugs [J].

Braña, MF ;

Cacho, M ;

Gradillas, A ;

de Pascual-Teresa, B ;

Ramos, A .

CURRENT PHARMACEUTICAL DESIGN, 2001, 7 (17) :1745-1780

[5] MICELLAR CATALYSIS OF ORGANIC-REACTIONS .29. SNAR REACTIONS WITH NEUTRAL NUCLEOPHILES [J].

BROXTON, TJ ;

MARCOU, V .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (03) :1041-1044

[6] Synthesis of N2 2′-deoxyguanosine adducts formed by 1-nitropyrene [J].

Chakraborti, D ;

Colis, L ;

Schneider, R ;

Basu, AK .

ORGANIC LETTERS, 2003, 5 (16) :2861-2864

[7]

CHEN MHG, 2000, Patent No. 2000064856

[8] Convenient access to substituted acridines by a Buchwald-Hartwig amination [J].

Csuk, R ;

Barthel, A ;

Raschke, C .

TETRAHEDRON, 2004, 60 (27) :5737-5750

[9] Interest of acridine derivatives in the anticancer chemotherapy [J].

Demeunynck, M ;

Charmantray, F ;

Martelli, A .

CURRENT PHARMACEUTICAL DESIGN, 2001, 7 (17) :1703-1724

[10] Antimalarial, antitrypanosomal, and antileishmanial activities and cytotoxicity of bis(9-amino-6-chloro-2-methoxyacridines):: Influence of the linker [J].

Girault, S ;

Grellier, P ;

Berecibar, A ;

Maes, L ;

Mouray, E ;

Lemière, P ;

Debreu, MA ;

Davioud-Charvet, E ;

Sergheraert, C .

JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (14) :2646-2654

← 1 2 3 4 5 →