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One-step furan ring formation: Synthesis of furo[3,2-h]quinolones

✍ Scribed by Masahiro Fujita; Hiroshi Egawa; Katsumi Chiba; Jun-Ichi Matsumoto

Publisher
Journal of Heterocyclic Chemistry
Year
1997
Tongue
English
Weight
363 KB
Volume
34
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

The one‐pot reaction of ethyl 1‐cyclopropyl‐6,7,8‐trifluoro‐1,4‐dihydro‐4‐oxoquinoline‐3‐carboxylate (6) with tert‐butyl acetoacetate gave 3‐tert‐butyl 7‐ethyl 9‐cyclopropyl‐4‐fluoro‐6,9‐dihydro‐2‐methyl‐6‐oxofuro[3,2‐h]quinoline‐3,7‐dicarboxylate (5). This regioselective cyclization was rationalized by the Hard and Soft Acids and Bases principle. By use of a similar furan‐forming reaction, we prepared 2‐(amino‐methyl)furo[3,2‐h]quinoline‐7‐carboxylic acid 4. Compound 4 showed weak antibacterial activity.

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