Synthetic Routes to Quinoline Derivatives: Novel Syntheses of 3-Butyryl-8-methoxy-4-[(2-methylphenyl)amino]quinoline and 3-Butyryl-8-(2-hydroxyethoxy)-4-[(2-methylphenyl)amino]quinoline

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• 作者：Richard J. Atkins ; Gary F. Breen ; Lynne P. Crawford ; Trevor J. Grinter ; Michael A. Harris ; Jerome F. Hayes ; Clive J. Moores ; Richard N. Saunders ; Andrew C. Share ; Timothy C. Walsgrove ; and Christopher
• 刊名：Organic Process Research & Development
• 出版年：1997
• 出版时间：May 1997
• 年：1997
• 卷：1
• 期：3
• 页码：185 - 197
• 全文大小：351K
• 年卷期：v.1,no.3(May 1997)
• ISSN：1520-586X

文摘

The 3,4,8-trisubstituted quinoline derivatives2-butyryl-8-methoxy-4-[(2-methylphenyl)amino]quinoline and3-butyryl-8-(2-hydroxyethoxy)-4-[(2-methylphenyl)amino]quinoline wereprepared using five novel synthetic strategies, each involvingadifferent disconnection as a basis for the key step. Onesuchstrategy led to the development of highly efficient processesforthe large-scale preparations of both compounds andfeatureda facile cyclisation of an [(arylamino)methylene]malonateandan unusual Reformatsky reaction of aquinoline-3-carboxylatewith tert-butyl 2-bromobutyrate in the presence ofzinc.