ChemInform Abstract: Use of 1,3-Dipolar Cycloaddition for the Synthesis of Novel Fluoroquinolones.

✍ Scribed by N. N. NAGIBINA; L. P. SIDOROVA; N. A. KLYUEV; V. N. CHARUSHIN; O. N. CHUPAKHIN

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 37 KB
• Volume: 29
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199833183

✦ Synopsis

Use of 1,3-Dipolar Cycloaddition for the Synthesis of Novel Fluoroquinolones.

-A novel synthetic way for the modification of 6-fluoroquinoline-4-one-3-carboxylic acids is presented. The 7-azido-derivative (II) undergoes 1,3-dipolar cycloaddition to several alkenes like norbornene, cyclopentenonorbornene, cycloalkenes, and alkynes in refluxing dioxane to give the corresponding 7-triazolyl derivatives. In some cases a subsequent elimination of nitrogen takes place to give 7-amino or 7-aziridinyl derivatives. An analogous reaction takes place with the 7-methylideneimine oxide derivative in situ formed from hydroxylamine (XII) to give on reaction with alkenes the 7oxazolylquinolones (XV). -(NAGIBINA, N.