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微波无溶剂条件下硫酸锆催化环氧化合物区域选择性开环合成氮杂核苷。

Synthesis of azanucleosides through regioselective ring-opening of epoxides catalyzed by sulphated zirconia under microwave and solvent-free conditions.

机构信息

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

出版信息

Molecules. 2012 Mar 15;17(3):3359-69. doi: 10.3390/molecules17033359.

DOI:10.3390/molecules17033359
PMID:22421790
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6268552/
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.

摘要

新型氮杂核苷通过硫酸锆（ZS）作为催化剂，在 1-烯丙基-3-（环氧乙烷-2-基甲基）嘧啶-2,4(1H,3H)-二酮和 1-烯丙基-5-甲基-3-（环氧乙烷-2-基甲基）嘧啶-2,4(1H,3H)-二酮与（S）-脯氨酸的亲核环氧化物开环反应中得到。新模板的产率较高，反应路线利用了硫酸锆作为催化剂存在时环氧化物的反应活性。关键步骤在微波和无溶剂条件下进行，具有高选择性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/25c3/6268552/6e2b255b6d0c/molecules-17-03359-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/25c3/6268552/388c53f59762/molecules-17-03359-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/25c3/6268552/90157537df71/molecules-17-03359-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/25c3/6268552/aaf59e9b7a34/molecules-17-03359-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/25c3/6268552/49fa286b1267/molecules-17-03359-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/25c3/6268552/8b369ce2fd41/molecules-17-03359-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/25c3/6268552/6e2b255b6d0c/molecules-17-03359-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/25c3/6268552/388c53f59762/molecules-17-03359-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/25c3/6268552/90157537df71/molecules-17-03359-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/25c3/6268552/aaf59e9b7a34/molecules-17-03359-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/25c3/6268552/49fa286b1267/molecules-17-03359-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/25c3/6268552/8b369ce2fd41/molecules-17-03359-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/25c3/6268552/6e2b255b6d0c/molecules-17-03359-g006.jpg

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