The neber approach to 2-(tetrazol-5-yl)-2 H-azirines

AL Cardoso, L Gimeno, A Lemos…

Index: Cardoso, Ana Lucia; Gimeno, Lourdes; Lemos, Americo; Palacios, Francisco; Pinho E Melo, Teresa M. V. D. Journal of Organic Chemistry, 2013 , vol. 78, # 14 p. 6983 - 6991

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Citation Number: 9

Abstract

The synthesis of 2-(tetrazol-5-yl)-2 H-azirines is reported for the first time. Using the Neber approach, β-ketoxime-1 H-tetrazoles were converted into the target 2 H-azirines bearing phenyl, furan-2-yl, thiophen-2-yl, or pyrrol-2-yl substituents at C-3. It was demonstrated that the alkaloid-mediated Neber reaction allows the asymmetric synthesis of 2-(tetrazol-5-yl)-2 H-azirines.

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