TY - JOUR
T1 - One-pot, microwave-assisted synthesis of polymethylene-bridged bis(1H-1,2,4-triazol-5(3)-amines) and their tautomerism
AU - Lim, Felicia Phei Lin
AU - Hu, Lee Ming
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:
© 2018 Elsevier Ltd
Copyright:
Copyright 2018 Elsevier B.V., All rights reserved.
PY - 2018/10/17
Y1 - 2018/10/17
N2 - A highly selective and efficient method for the synthesis of 3,3′(5,5′)-polymethylene-bis(1H-1,2,4-triazol-5(3)-amines) was developed using the reaction of dicarboxylic acids and aminoguanidine in an aqueous medium. This one-pot, microwave-promoted method was proved to be scalable affording the desired products in good yields and purity. The scope of the method was successfully explored by the preparation of a small library of polymethylene-bis(1H-1,2,4-triazol-5(3)-amines) with different alkyl chain linkers. The annular prototropic tautomerism in the prepared compounds was studied using NMR spectroscopy and X-ray crystallography.
AB - A highly selective and efficient method for the synthesis of 3,3′(5,5′)-polymethylene-bis(1H-1,2,4-triazol-5(3)-amines) was developed using the reaction of dicarboxylic acids and aminoguanidine in an aqueous medium. This one-pot, microwave-promoted method was proved to be scalable affording the desired products in good yields and purity. The scope of the method was successfully explored by the preparation of a small library of polymethylene-bis(1H-1,2,4-triazol-5(3)-amines) with different alkyl chain linkers. The annular prototropic tautomerism in the prepared compounds was studied using NMR spectroscopy and X-ray crystallography.
KW - CIALMEYJVQCAPV-UHFFFAOYSA-N
KW - Dicarboxylic acid
KW - GFIDVFDVBPKVEL-UHFFFAOYSA-N
KW - GNAZDVZJXQCLPG-UHFFFAOYSA-N
KW - HDYKKZCPRXWZJW-UHFFFAOYSA-N
KW - ITLLBMUFIIWUFW-UHFFFAOYSA-N
KW - JVHWVLLANDAWPO-UHFFFAOYSA-N
KW - Microwave-assisted synthesis
KW - One-pot synthesis
KW - RRIQYSBGTNWGDO-UHFFFAOYSA-N
KW - SIDSWGCUQHPXDB-UHFFFAOYSA-N
KW - Tautomerism
KW - Triazole
UR - http://www.scopus.com/inward/record.url?scp=85053122470&partnerID=8YFLogxK
U2 - 10.1016/j.tetlet.2018.09.018
DO - 10.1016/j.tetlet.2018.09.018
M3 - Article
AN - SCOPUS:85053122470
SN - 0040-4039
VL - 59
SP - 3792
EP - 3796
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 42
ER -