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ChemInform Abstract: Molecular Rearrangements of 1,2,3-Triazoline — Adducts of 7-Azido-6-fluoroquinol-4-ones with Alkenes.

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

Publisher
John Wiley and Sons
Year
2010
Weight
40 KB
Volume
29
Category
Article
ISSN
0931-7597

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✦ Synopsis

Molecular Rearrangements of 1,2,3-Triazoline -Adducts of 7-Azido-6-fluoroquinol-4-ones with Alkenes.

-7-Azido-6-fluoroquinolone (I) undergoes 1,3-dipolar cycloaddition with enamines of cyclic ketones (II) to furnish the fused triazole derivatives (III) in good to excellent yields. Cycloadducts derived from cycloheptanone and cyclohexanone enamine undergo an azo-pinacol rearrangement on heating to afford amidine derivatives with ring-contracted cycloalkane fragment, (IV) and (V), respectively.The triazole adduct of (I) with norbornene undergoes in situ molecular rearrangement to give the 7-amino derivative (IX), while the adduct derived from (I) and 5-hydroxymethylnorbornene (VI) suffers a complex cationic rearrangement accompanied by an intramolecular cyclization involving the hydroxymethyl group [→(VII)]. -(NAGIBINA, N.

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