Alkylation of 1-[N-(Hydroxymethyl)-N-methylamino]-4-quinolones. An Improved Preparation of Intermediates for Novel Potent Tricyclic Quinolone Antibacterial Agents

A new and improved method for the preparation of the key cyclization precursors for novel pyrido[3,2,1-ij]cinnoline antibacterial agents that avoids the use of di-t-butyl methylenemalonate is described. The key process is the alkylation of 1-[N-(hydroxymethyl)-N-methylamino]-4-quinolones with di-t-b...

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Published inBulletin of the Chemical Society of Japan Vol. 69; no. 5; pp. 1371 - 1376
Main Authors Barrett, David, Sasaki, Hiroshi, Kinoshita, Takayoshi, Tsutsumi, Hideo, Sakane, Kazuo
Format Journal Article
LanguageEnglish
Published TOKYO The Chemical Society of Japan 01.05.1996
Chemical Soc Japan
Chemical Society of Japan
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
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Summary:A new and improved method for the preparation of the key cyclization precursors for novel pyrido[3,2,1-ij]cinnoline antibacterial agents that avoids the use of di-t-butyl methylenemalonate is described. The key process is the alkylation of 1-[N-(hydroxymethyl)-N-methylamino]-4-quinolones with di-t-butyl malonate via the intermediate chloromethyl derivatives. Unexpectedly, this process produced labile pyrazolo[1,5-a]quinoline derivatives that were subsequently shown to undergo ring opening and cyclization to C8 to produce the pyrido[3,2,1-ij]cinnoline key intermediates.
ISSN:0009-2673
1348-0634
DOI:10.1246/bcsj.69.1371