Synthesis of fused tetrazolone derivatives

Key Findings & Data:Treatment of anhydrides with trimethylsilyl azide opened the lactone rings and formed the corresponding intermediates, which bore 1,3-dipole and dipolarophile functionalities in ortho positions.

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Conclusion & Impact:When the carbonyl groups in anhydride were not conjugated with any double bond, then a triazine-fused tetrazolone derivative was formed.

🔬Design:Research Article

📍Scope:Comprehensive Sample

⚙️Variables:Tetrazolone · acyl azide · Curtius rearrangement

Abstract

New fused tetrazolone derivatives were synthesized using homophthalic and maleic anhydrides. Treatment of anhydrides with trimethylsilyl azide opened the lactone rings and formed the corresponding intermediates, which bore 1,3-dipole and dipolarophile functionalities in ortho positions. The intermediates partially underwent internal 1,3-dipolar cycloaddition to produce fused tetrazolone derivatives. When the carbonyl groups in anhydride were not conjugated with any double bond, then a triazine-fused tetrazolone derivative was formed.

Özet

New fused tetrazolone derivatives were synthesized using homophthalic and maleic anhydrides. Treatment of anhydrides with trimethylsilyl azide opened the lactone rings and formed the corresponding intermediates, which bore 1,3-dipole and dipolarophile functionalities in ortho positions. The intermediates partially underwent internal 1,3-dipolar cycloaddition to produce fused tetrazolone derivatives. When the carbonyl groups in anhydride were not conjugated with any double bond, then a triazine-fused tetrazolone derivative was formed.

Keywords

Tetrazolone acyl azide Curtius rearrangement 3-dipole dipolarophile 3-dipolar cycloaddition

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Cite This Article

ÖZCAN, S., EKMEKÇİ, Z., MÜJDE, B., BALCI, M. (2013). Synthesis of fused tetrazolone derivatives. Turkish Journal of Chemistry, Cilt: 37 - Sayı: 4, 610–618. https://ajindex.com/articles/184759

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References (1)

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