✦ LIBER ✦

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

✍ Scribed by Ramiya R. Amaresh; Paramasivan T. Perumal

Book ID: 104208925
Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 784 KB
Volume: 54
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(98)00887-4

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✦ Synopsis

Studies have been carried out on a new novel method for the synthesis of 2-(N,Ndisubstituted)aminoquinoline via intramolecular electrophilic substitution of methyleniminium salts by azide. Treatment of l-(2-azidophenyl)ethanone with Vilsmeier reagent (DMF/POC13) gave 4-chloro-2dimethylamino-3-quinolinecarboxaldehyde and 4-chloro-2 -dimethylaminoquinoline, whereas 1 -(2azidophenyl)propanone and 1-(2-azidophenyl)butanone give unformylated products 4-chloro-3-methyl-2dimethylaminoquinoline, 4-chloro-3-methylquinoline and 4-chloro-3-ethyl-2-dimethylaminoquinoline, 4chloro-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 stericaUy hindered Nmethylformanilide(MFA), N-formylpiperidine(NFP) and N-formylmorpholine(NFM) instead of DMF.

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