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Molecules 2012, 17(3), 3359-3369; doi:10.3390/molecules17033359
Article

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

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Received: 10 February 2012; in revised form: 7 March 2012 / Accepted: 9 March 2012 / Published: 15 March 2012
(This article belongs to the Section Organic Synthesis)
Download PDF [272 KB, uploaded 18 June 2014]
Abstract: 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.
Keywords: azanucleosides; sulphated zirconia; nucleophilic reaction; regioselective reaction; epoxide’s ring-opening; microwave azanucleosides; sulphated zirconia; nucleophilic reaction; regioselective reaction; epoxide’s ring-opening; microwave
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Hernández-Reyes, C.X.; Angeles-Beltrán, D.; Lomas-Romero, L.; González-Zamora, E.; Gaviño, R.; Cárdenas, J.; Morales-Serna, J.A.; Negrón-Silva, G.E. Synthesis of Azanucleosides through Regioselective Ring-Opening of Epoxides Catalyzed by Sulphated Zirconia under Microwave and Solvent-Free Conditions. Molecules 2012, 17, 3359-3369.

AMA Style

Hernández-Reyes CX, Angeles-Beltrán D, Lomas-Romero L, González-Zamora E, Gaviño R, Cárdenas J, Morales-Serna JA, Negrón-Silva GE. Synthesis of Azanucleosides through Regioselective Ring-Opening of Epoxides Catalyzed by Sulphated Zirconia under Microwave and Solvent-Free Conditions. Molecules. 2012; 17(3):3359-3369.

Chicago/Turabian Style

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. 2012. "Synthesis of Azanucleosides through Regioselective Ring-Opening of Epoxides Catalyzed by Sulphated Zirconia under Microwave and Solvent-Free Conditions." Molecules 17, no. 3: 3359-3369.


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