Synthesis of New Functionally Substituted 1-R-tetrazoles and Their 5-Amino Derivatives

• Published in: Chemistry of heterocyclic compounds (New York, N.Y. 1965) Vol. 41; no. 8; pp. 999 - 1004
• Main Authors: Voitekhovich, S. V., Vorob'ev, A. N., Gaponik, P. N., Ivashkevich, O. A.
• Format: Journal Article
• Language: English
• Published: New York Springer Nature B.V 01-08-2005
• Subjects: Amines; Organic compounds; Sodium azides; Substitutes; Tetrazoles
• ISSN: 0009-3122; 1573-8353
• DOI: 10.1007/s10593-005-0267-4

It has been shown that amino derivatives of sulfanilamide, and also some functionally substituted primary arylamines and cycloalkylamines, undergo heterocyclization with triethyl orthoformate and sodium azide with the formation of 1-monosubstituted tetrazoles. Primary amines of the azole series, 5-aminotetrazole, 5-amino-1-methyltetrazole, 4-amino-1,2,4-triazole, and also less basic arylamines (4-fluoro-3-nitroaniline, 2,6-dibromo-4-nitroaniline) did not react. An efficient method of introducing an amino group into position C(5) of the tetrazole ring of 1-aryltetrazoles is proposed, based on alkaline decomposition of the tetrazole ring and heterocyclization of the resulting N-arylcyanamides on interaction with ammonium azide generated in situ.