A novel one-pot synthesis of 2-aminoquinolines from arylazidoketones by cyclization under Vilsmeier conditions

被引：24

作者：

Amaresh, RR ^{[1
]}

Perumal, PT ^{[1
]}

机构：

[1] Cent Leather Res Inst, Div Organ Chem, Adyar 600020, Chennai, India

来源：

TETRAHEDRON | 1998年 / 54卷 / 47期

关键词：

iminium salt; quinolines; Vilsmeier reagent;

D O I：

10.1016/S0040-4020(98)00887-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Studies have been carried out on a new novel method for the synthesis of 2-(N,N-disubstituted)aminoquinoline via intramolecular electrophilic substitution of methyleniminium salts by azide. Treatment of 1-(2-azidophenyl)ethanone with Vilsmeier reagent (DMF/POCl3) gave 4-chloro-2-dimethylamino-3-quinolinecarboxaldehyde and 4-chloro-2-dimethylaminoquinoline, whereas 1-(2-azidophenyl)propanone and 1-(2-azidophenyl)butanone give unformylated products 4-chloro-3-methyl-2-dimethylaminoquinoline, 4-chloro-3-methylquinoline and 4-chloro-3-ethyl-2-dimethylaminoquinolin 4-chloro-3-ethylquinoline respectively. The possible mechanisms for the formation of the products are discussed. The effect of the N,N-dimethylamino leaving group has been studied using sterically hindered N-methylformanilide(MFA), N-formylpiperidine(NFP) and N-formylmorpholine(NFM) instead of DMF. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：14327 / 14340

页数：14

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