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Paper | Regular issue | Vol 100, No. 11, 2020, pp.1816-1830
Published online, 26th August, 2020
DOI: 10.3987/COM-20-14321
Facile Preparation of 5-Alkyl-1-aryltetrazoles with Arenes, Acyl Chlorides, Hydroxylamine, and Diphenylphosphoryl Azide

Kaho Shibasaki and Hideo Togo*

*Graduate School of Sciences, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan


Successive treatment of arenes with acyl chlorides and AlCl3, the addition of water and removal of solvent, the reaction with NH2OH•HCl and K2CO3, and the reaction with diphenylphosphoryl azide and DBU under warming conditions gave the corresponding 5-alkyl-1-aryltetrazoles efficiently in good to moderate yields. The present method is one-pot transformation of arenes into 5-alkyl-1-aryltetrazoles using the Friedel-Crafts acylation and the Beckmann rearrangement under transition-metal-free conditions.