Synthesis of Azanucleosides through Regioselective Ring-Opening of Epoxides Catalyzed by Sulphated Zirconia under Microwave and Solvent-Free Conditions

New azanucleosides were obtained using sulphated zirconia (ZS) as catalyst in the nucleophilic oxirane ring opening reaction of 1-allyl-3-(oxiran-2-ylmethyl)pyrimidine-2,4(1H,3H)-dione and 1-allyl-5-methyl-3-(oxiran-2-ylmethyl)-pyrimidine-2,4(1H,3H)-dione, with (S)-prolinol. The new templates were o...

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Autores principales: Hernández-Reyes, Celia Xochitl, Angeles-Beltrán, Deyanira, Lomas-Romero, Leticia, González-Zamora, Eduardo, Gaviño, Rubén, Cárdenas, Jorge, Morales-Serna, José Antonio, Negrón-Silva, Guillermo E.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2012
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Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268552/
https://www.ncbi.nlm.nih.gov/pubmed/22421790
http://dx.doi.org/10.3390/molecules17033359
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author Hernández-Reyes, Celia Xochitl
Angeles-Beltrán, Deyanira
Lomas-Romero, Leticia
González-Zamora, Eduardo
Gaviño, Rubén
Cárdenas, Jorge
Morales-Serna, José Antonio
Negrón-Silva, Guillermo E.
author_facet Hernández-Reyes, Celia Xochitl
Angeles-Beltrán, Deyanira
Lomas-Romero, Leticia
González-Zamora, Eduardo
Gaviño, Rubén
Cárdenas, Jorge
Morales-Serna, José Antonio
Negrón-Silva, Guillermo E.
author_sort Hernández-Reyes, Celia Xochitl
collection PubMed
description New azanucleosides were obtained using sulphated zirconia (ZS) as catalyst in the nucleophilic oxirane ring opening reaction of 1-allyl-3-(oxiran-2-ylmethyl)pyrimidine-2,4(1H,3H)-dione and 1-allyl-5-methyl-3-(oxiran-2-ylmethyl)-pyrimidine-2,4(1H,3H)-dione, with (S)-prolinol. The new templates were obtained with good yields following a route which exploits the reactivity of epoxides in the presence of sulphated zirconia as catalyst. The key step was carried out using microwave and solvent-free conditions and proceeds with high selectivity.
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spelling pubmed-62685522018-12-20 Synthesis of Azanucleosides through Regioselective Ring-Opening of Epoxides Catalyzed by Sulphated Zirconia under Microwave and Solvent-Free Conditions Hernández-Reyes, Celia Xochitl Angeles-Beltrán, Deyanira Lomas-Romero, Leticia González-Zamora, Eduardo Gaviño, Rubén Cárdenas, Jorge Morales-Serna, José Antonio Negrón-Silva, Guillermo E. Molecules Article New azanucleosides were obtained using sulphated zirconia (ZS) as catalyst in the nucleophilic oxirane ring opening reaction of 1-allyl-3-(oxiran-2-ylmethyl)pyrimidine-2,4(1H,3H)-dione and 1-allyl-5-methyl-3-(oxiran-2-ylmethyl)-pyrimidine-2,4(1H,3H)-dione, with (S)-prolinol. The new templates were obtained with good yields following a route which exploits the reactivity of epoxides in the presence of sulphated zirconia as catalyst. The key step was carried out using microwave and solvent-free conditions and proceeds with high selectivity. MDPI 2012-03-15 /pmc/articles/PMC6268552/ /pubmed/22421790 http://dx.doi.org/10.3390/molecules17033359 Text en © 2012 by the authors; licensee MDPI, Basel, Switzerland. http://creativecommons.org/licenses/by/3.0/ This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Hernández-Reyes, Celia Xochitl
Angeles-Beltrán, Deyanira
Lomas-Romero, Leticia
González-Zamora, Eduardo
Gaviño, Rubén
Cárdenas, Jorge
Morales-Serna, José Antonio
Negrón-Silva, Guillermo E.
Synthesis of Azanucleosides through Regioselective Ring-Opening of Epoxides Catalyzed by Sulphated Zirconia under Microwave and Solvent-Free Conditions
title Synthesis of Azanucleosides through Regioselective Ring-Opening of Epoxides Catalyzed by Sulphated Zirconia under Microwave and Solvent-Free Conditions
title_full Synthesis of Azanucleosides through Regioselective Ring-Opening of Epoxides Catalyzed by Sulphated Zirconia under Microwave and Solvent-Free Conditions
title_fullStr Synthesis of Azanucleosides through Regioselective Ring-Opening of Epoxides Catalyzed by Sulphated Zirconia under Microwave and Solvent-Free Conditions
title_full_unstemmed Synthesis of Azanucleosides through Regioselective Ring-Opening of Epoxides Catalyzed by Sulphated Zirconia under Microwave and Solvent-Free Conditions
title_short Synthesis of Azanucleosides through Regioselective Ring-Opening of Epoxides Catalyzed by Sulphated Zirconia under Microwave and Solvent-Free Conditions
title_sort synthesis of azanucleosides through regioselective ring-opening of epoxides catalyzed by sulphated zirconia under microwave and solvent-free conditions
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268552/
https://www.ncbi.nlm.nih.gov/pubmed/22421790
http://dx.doi.org/10.3390/molecules17033359
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