TY - JOUR
T1 - A synthesis of new 7-amino-substituted 4-aminopyrazolo[1,5-a][1,3,5]triazines via a selective three-component triazine ring annulation
AU - Lim, Felicia Phei Lin
AU - Luna, Giuseppe
AU - Tan, Khai Ching
AU - Tiekink, Edward R.T.
AU - Dolzhenko, Anton V.
N1 - Funding Information:
The Research Centre for Crystalline Materials (Sunway University) is thanked for the X-ray intensity data. This work is supported by the Ministry of Higher Education, Malaysia under Fundamental Research Grant Scheme, grant number FRGS/1/2015/SG01/MUSM/03/1.
Funding Information:
The Research Centre for Crystalline Materials (Sunway University) is thanked for the X-ray intensity data. This work is supported by the Ministry of Higher Education, Malaysia under Fundamental Research Grant Scheme, grant number FRGS/1/2015/SG01/MUSM/03/1 .
Publisher Copyright:
© 2019 Elsevier Ltd
Copyright:
Copyright 2019 Elsevier B.V., All rights reserved.
PY - 2019/4/12
Y1 - 2019/4/12
N2 - 3-Amino-substituted 5-aminopyrazoles were found to be suitable substrates for the synthesis of new 4-aminopyrazolo[1,5-a][1,3,5]triazines (5-aza-9-deaza-adenines) when used in the one-pot, three-component reaction with cyanamide and triethyl orthoformate under microwave irradiation. The reaction proceeded selectively and its scope was demonstrated by the preparation of a library of 4-aminopyrazolo[1,5-a][1,3,5]triazines. Some structural aspects of the prepared compounds were investigated using dynamic NMR spectroscopy and X-ray crystallography. The operational simplicity, short reaction time, and good reproducibility are attractive features of the developed robust and practical approach for the synthesis of 7-amino-substituted 4-aminopyrazolo[1,5-a][1,3,5]triazines.
AB - 3-Amino-substituted 5-aminopyrazoles were found to be suitable substrates for the synthesis of new 4-aminopyrazolo[1,5-a][1,3,5]triazines (5-aza-9-deaza-adenines) when used in the one-pot, three-component reaction with cyanamide and triethyl orthoformate under microwave irradiation. The reaction proceeded selectively and its scope was demonstrated by the preparation of a library of 4-aminopyrazolo[1,5-a][1,3,5]triazines. Some structural aspects of the prepared compounds were investigated using dynamic NMR spectroscopy and X-ray crystallography. The operational simplicity, short reaction time, and good reproducibility are attractive features of the developed robust and practical approach for the synthesis of 7-amino-substituted 4-aminopyrazolo[1,5-a][1,3,5]triazines.
KW - Aza-adenine
KW - Azapurine
KW - Microwave-assisted synthesis
KW - Multicomponent reaction
KW - One-pot synthesis
KW - Pyrazole
KW - Restricted rotation
KW - Triazine
UR - http://www.scopus.com/inward/record.url?scp=85062732209&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2019.03.002
DO - 10.1016/j.tet.2019.03.002
M3 - Article
AN - SCOPUS:85062732209
SN - 0040-4020
VL - 75
SP - 2322
EP - 2329
JO - Tetrahedron
JF - Tetrahedron
IS - 15
ER -