Journal
TETRAHEDRON
Volume 64, Issue 49, Pages 11041-11049Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2008.09.089
Keywords
Heterocycles; Cyclocondensations; Selective multicomponent reactions; Microwave-assisted organic synthesis; Ultrasonic-promoted reactions; Phenylpyruvic acid; Aminoazoles
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Funding
- INTAS [04-83-2844]
- DAAD Euler scholarship
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The multicomponent reactions of 3-amino-1,2,4-triazoles/5-aminotetrazole with phenylpyruvic acids and aromatic aldehydes were studied using conventional thermal heating, ultrasonification and microwave dielectric heating. Two different reaction pathways for these cyclocondensations occurring under either kinetic or thermodynamic control were established depending on the temperature regime and building block selection. In case of aminotriazoles, an unprecedented reaction pathway leading to 5-aryl-7-hydroxy-6-phenyl-4,5,6,7-tetrahydro [1,2,4]triazolol [1,5-a]pyrimidine-7-carboxylic acids was found and discussed. (C) 2008 Elsevier Ltd. All rights reserved.
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