AlCl₃ as an Effective Lewis Acid for the Synthesis of Arylaminotetrazoles

Abstract

An efficient method for preparation of the arylaminotetrazoles derivatives is reported using aluminium chloride as an effective Lewis acid. Generally, 5-arylamino-1H-tetrazole isomer can be obtained from arylcyanamides carrying electron-withdrawing substituents on the aryl ring. As the electropositivity of the substituent is increased, the product is shifted toward the formation of 1-aryl-5-amino-1H-tetrazole isomer.

Keywords:

• AlCl₃
• 5-arylamino-1H-tetrazole
• 1-aryl-5-amino-1H-tetrazole
• arylcyanamide
• Lewis acid

ACKNOWLEDGMENT

The authors are thankful to the Bu-Ali Sina University for the partial support of this work.

Notes

^a Yield refers to pure isolated products.

^a Isolated yield.

^b Under solvent-free and thermal conditions at 80 °C.

^c Glacial acetic acid as both solvent and proton donor source.

^d Room temperature.