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

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...

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Bibliographic Details
Main Authors: Guillermo E. Negrón-Silva, José Antonio Morales-Serna, Jorge Cárdenas, Rubén Gaviño, Leticia Lomas-Romero, Celia Xochitl Hernández-Reyes, Eduardo González-Zamora, Deyanira Angeles-Beltrán
Format: Article
Language:English
Published: MDPI AG 2012-03-01
Series:Molecules
Subjects:
azanucleosides
sulphated zirconia
nucleophilic reaction
regioselective reaction
epoxide’s ring-opening
microwave
Online Access:http://www.mdpi.com/1420-3049/17/3/3359/
Description
Summary: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.
ISSN:1420-3049

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