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

Authors

ALI REZA MODARRESI-ALAM
MAHMOUD NASROLLAHZADEH

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.

DOI

10.3906/kim-0808-44

Keywords

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

First Page

267

Last Page

280

Recommended Citation

MODARRESI-ALAM, ALI REZA and NASROLLAHZADEH, MAHMOUD (2009) "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," Turkish Journal of Chemistry: Vol. 33: No. 2, Article 10. https://doi.org/10.3906/kim-0808-44
Available at: https://journals.tubitak.gov.tr/chem/vol33/iss2/10