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 : 15 | Download : 5

Publication Date : 0000-00-00

Article Type : Research Paper

Abstract :A simple and efficient method for the preparation of 5-arylamino-1H insert ignore into journalissuearticles values(2H);-tetrazoles insert ignore into journalissuearticles values(3a-i); and 5-amino-1-ary-1H-tetrazoles insert ignore into journalissuearticles values(4a-i);, with excellent yields and high purity, from secondary arylcyanamides insert ignore into journalissuearticles values(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 insert ignore into journalissuearticles values(-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