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One-pot,microwave-assisted synthesis of polymethylene-bridged bis(1H-1,2,4-triazol-5(3)-amines) and their tautomerism
Authors:Felicia Phei Lin Lim  Lee Ming Hu  Edward R.T. Tiekink  Anton V. Dolzhenko
Affiliation:1. School of Pharmacy, Monash University Malaysia, Jalan Lagoon Selatan, Bandar Sunway, Selangor Darul Ehsan 47500, Malaysia;2. Research Centre for Crystalline Materials, School of Science and Technology, Sunway University, Bandar Sunway, Selangor Darul Ehsan 47500, Malaysia;3. School of Pharmacy and Biomedical Sciences, Curtin Health Innovation Research Institute, Faculty of Health Sciences, Curtin University, GPO Box U1987, Perth, Western Australia 6845, Australia
Abstract: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.
Keywords:ITLLBMUFIIWUFW-UHFFFAOYSA-N  ITLLBMUFIIWUFW-UHFFFAOYSA-N  ITLLBMUFIIWUFW-UHFFFAOYSA-N  SIDSWGCUQHPXDB-UHFFFAOYSA-N  SIDSWGCUQHPXDB-UHFFFAOYSA-N  SIDSWGCUQHPXDB-UHFFFAOYSA-N  RRIQYSBGTNWGDO-UHFFFAOYSA-N  RRIQYSBGTNWGDO-UHFFFAOYSA-N  RRIQYSBGTNWGDO-UHFFFAOYSA-N  CIALMEYJVQCAPV-UHFFFAOYSA-N  CIALMEYJVQCAPV-UHFFFAOYSA-N  CIALMEYJVQCAPV-UHFFFAOYSA-N  GNAZDVZJXQCLPG-UHFFFAOYSA-N  GNAZDVZJXQCLPG-UHFFFAOYSA-N  GNAZDVZJXQCLPG-UHFFFAOYSA-N  HDYKKZCPRXWZJW-UHFFFAOYSA-N  HDYKKZCPRXWZJW-UHFFFAOYSA-N  HDYKKZCPRXWZJW-UHFFFAOYSA-N  GFIDVFDVBPKVEL-UHFFFAOYSA-N  GFIDVFDVBPKVEL-UHFFFAOYSA-N  GFIDVFDVBPKVEL-UHFFFAOYSA-N  JVHWVLLANDAWPO-UHFFFAOYSA-N  JVHWVLLANDAWPO-UHFFFAOYSA-N  JVHWVLLANDAWPO-UHFFFAOYSA-N  Triazole  Dicarboxylic acid  Microwave-assisted synthesis  One-pot synthesis  Tautomerism
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