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

Molecules

Celia Xochitl Hernández-Reyes¹  Deyanira Angeles-Beltrán¹  Leticia Lomas-Romero¹  Eduardo González-Zamora¹  Rubén Gaviño¹  Jorge Cárdenas¹  José Antonio Morales-Serna¹ 

[1] ¹Departamento de Ciencias Básicas, Universidad Autónoma Metropolitana, Av. San Pablo No. 180, México D.F., C.P. 02200, Mexico

关键词: azanucleosides;    sulphated zirconia;    nucleophilic reaction;    regioselective reaction;    epoxide’s ring-opening;    microwave;   

DOI  :  10.3390/molecules17033359

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.