A Facile Synthesis of 4-Tetrazolyl-Substituted 4H-3,1-Benzoxazines through Sequential Passerini-Azide/Acylation/Catalytic Aza-Wittig Reaction

Abstract

A facile synthesis of 4-tetrazolyl-4H-3,1-benzoxazines by a Passerini-azide/acylation/catalytic aza-Wittig sequence was developed. The Passerini-azide reactions of 2-azidobenzaldehydes, trimethylsilyl azide and isocyanides produced tetrazoles, which were further acylated to give the azides in 28–74% overall yields. The catalytic aza-Wittig reactions of the azides generated 4-tetrazolyl-4H-3,1-benzoxazines in good yields, by using a catalytic amount of 3-methyl-1-phenyl phospholene-1-oxide (10 mol%) and TMDS/Ti(i-PrO)₄ reductant system.

Key words

tetrazole - 4H-3,1-benzoxazine - Passerini-azide reaction - catalytic aza-Wittig reaction - acylation

• References

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