Publikation: Multicomponent cyclocondensation reactions of aminoazoles, arylpyruvic acids and aldehydes with controlled chemoselectivity
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Datum
2008
Autor:innen
Sakhno, Yana I.
Desenko, Sergey M.
Shishkina, Svetlana V.
Shishkin, Oleg V.
Sysoyev, Dmytro O.
Kappe, C. Oliver
Chebanov, Valentin A.
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Tetrahedron. 2008, 64(49), pp. 11041-11049. ISSN 0040-4020. Available under: doi: 10.1016/j.tet.2008.09.089
Zusammenfassung
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]triazolo[1,5-a]pyrimidine-7-carboxylic acids was found and discussed.
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540 Chemie
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heterocycles, cyclocondensations, selective multicomponent reactions, microwave-assisted organic synthesis, ultrasonic-promoted reactions
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SAKHNO, Yana I., Sergey M. DESENKO, Svetlana V. SHISHKINA, Oleg V. SHISHKIN, Dmytro O. SYSOYEV, Ulrich GROTH, C. Oliver KAPPE, Valentin A. CHEBANOV, 2008. Multicomponent cyclocondensation reactions of aminoazoles, arylpyruvic acids and aldehydes with controlled chemoselectivity. In: Tetrahedron. 2008, 64(49), pp. 11041-11049. ISSN 0040-4020. Available under: doi: 10.1016/j.tet.2008.09.089BibTex
@article{Sakhno2008Multi-1041,
year={2008},
doi={10.1016/j.tet.2008.09.089},
title={Multicomponent cyclocondensation reactions of aminoazoles, arylpyruvic acids and aldehydes with controlled chemoselectivity},
number={49},
volume={64},
issn={0040-4020},
journal={Tetrahedron},
pages={11041--11049},
author={Sakhno, Yana I. and Desenko, Sergey M. and Shishkina, Svetlana V. and Shishkin, Oleg V. and Sysoyev, Dmytro O. and Groth, Ulrich and Kappe, C. Oliver and Chebanov, Valentin A.}
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<dcterms:abstract xml:lang="eng">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]triazolo[1,5-a]pyrimidine-7-carboxylic acids was found and discussed.</dcterms:abstract>
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