Synthesis of 5-Arylamino-1H (2H)-tetrazoles and 5-Amino-1-aryl-1H-tetrazoles from Secondary Arylcyanamides in Glacial Acetic Acid: A Simple and Efficient Method


Abstract: A simple and efficient method for the preparation of 5-arylamino-1H (2H)-tetrazoles (3a-i) and 5-amino-1-ary-1H-tetrazoles (4a-i), with excellent yields and high purity, from secondary arylcyanamides (1a-i) at room temperature in glacial acetic acid is described. Tautomers 3a-i were separated from tautomers 4a-i by crystallization in ethanol. A mechanism was introduced in glacial acetic acid. The ratio of isomers is described based on the electronic and steric effects of various substituents. The electron withdrawing group (-NO_2) increased the ratio of 4:3. The rate of product formation was enhanced by introducing electron donating substituents. ^1H-NMR and ^{13}C-NMR chemical shifts and multiplicities are also discussed.

Keywords: 5-Arylamino-1H (2H)-tetrazoles, 5-amino-1-aryl-1H-tetrazoles, arylcyanamides, guanyl azides, glacial acetic acid

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