Next Article in Journal
Oxime Esters of 2,6-Diazaanthracene-9,10-dione and 4,5-Diazafluoren-9-one as Photo-induced DNA-Cleaving Agents
Previous Article in Journal
Synthesis of Tetrasubstituted Alkenes via Metathesis
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

1
, 1
, 2
, 2
, 3
, 3
, 3
 and 1,*
1 Departamento de Ciencias Básicas, Universidad Autónoma Metropolitana, Av. San Pablo No. 180, México D.F., C.P. 02200, Mexico 2 Departamento de Química, Universidad Autónoma Metropolitana, Av. San Rafael Atlixco No. 186, México D.F., C.P. 09340, Mexico 3 Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, México D.F. 04510, Mexico
* Author to whom correspondence should be addressed.
Received: 10 February 2012 / Revised: 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.

Share & Cite This Article

Export to BibTeX |
EndNote


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.

View more citation formats

Related Articles

Article Metrics

Comments

Citing Articles

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert