- Turkish Journal of Chemistry
- Vol: 33 Issue: 2
- Synthesis of 5-Arylamino-1H (2H)-tetrazoles and 5-Amino-1-aryl-1H-tetrazoles from Secondary Arylcyan...
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 And Mahmoud Nasrollahzadeh
Pages : 267-280
View : 9 | Download : 3
Publication Date : 9999-12-31
Article Type : Makaleler
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 (-NO2) increased the ratio of 4:3. The rate of product formation was enhanced by introducing electron donating substituents. 1H-NMR and 13C-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