TY - JOUR
T1 - A convenient method for the synthesis of 7-amino-substituted 1,2,4-triazolo[1,5-a][1,3,5]triazin-5-amines
AU - Dolzhenko, Anton V.
AU - Pastorin, Giorgia
AU - Dolzhenko, Anna V.
AU - Chui, Wai Keung
N1 - Funding Information:
This work is supported by the National Medical Research Council, Singapore (NMRC/NIG/0020/2008) and the National University of Singapore (R-148-050-091-101/133 and R-148-000-069-112). The authors thank Koh Lip Lin, Tan Geok Kheng and Woo Su Fen for the X-ray crystallography study.
Copyright:
Copyright 2008 Elsevier B.V., All rights reserved.
PY - 2008/12/8
Y1 - 2008/12/8
N2 - A new practical synthesis of 7-amino-substituted 1,2,4-triazolo[1,5-a][1,3,5]triazin-5-amines is developed. The triazine ring closure of 5-guanidino-3-phenyl-1,2,4-triazole with trichloroacetonitrile proceeds chemo- and regioselectively depending on the nature of the solvent. Conducting the reaction in toluene provided 7-trichloromethyl-1,2,4-triazolo[1,5-a][1,3,5]triazin-5-amine as the product, which can be further aminated efficiently with replacement of the trichloromethyl group.
AB - A new practical synthesis of 7-amino-substituted 1,2,4-triazolo[1,5-a][1,3,5]triazin-5-amines is developed. The triazine ring closure of 5-guanidino-3-phenyl-1,2,4-triazole with trichloroacetonitrile proceeds chemo- and regioselectively depending on the nature of the solvent. Conducting the reaction in toluene provided 7-trichloromethyl-1,2,4-triazolo[1,5-a][1,3,5]triazin-5-amine as the product, which can be further aminated efficiently with replacement of the trichloromethyl group.
UR - http://www.scopus.com/inward/record.url?scp=54449102104&partnerID=8YFLogxK
U2 - 10.1016/j.tetlet.2008.10.003
DO - 10.1016/j.tetlet.2008.10.003
M3 - Article
AN - SCOPUS:54449102104
VL - 49
SP - 7180
EP - 7183
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 50
ER -