Selective S-Allylic Alkylation of 2-Thiopyrimidine with Morita-Baylis-Hillman Carbonates

doi:10.6023/cjoc201702015

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (8): 2078-2085.DOI: 10.6023/cjoc201702015 Previous Articles Next Articles

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2-巯基嘧啶与碳酸Morita-Baylis-Hillman酯的选择性S-烯丙基烷基化

杨靖亚^a, 李娜娜^a, 周红艳^b, 李天媛^a, 谢栋泰^a, 李政^a

a 西北师范大学化学化工学院兰州 730070;
b 甘肃农业大学理学院兰州 730070

收稿日期:2017-02-14 修回日期:2017-03-24 发布日期:2017-04-13
通讯作者: 杨靖亚 E-mail:yangjy@nwnu.edu.cn
基金资助:
国家自然科学基金（Nos.21362034，21462038）和高等学校博士学科点专项科研基金（No.20136203120005）资助项目.

Selective S-Allylic Alkylation of 2-Thiopyrimidine with Morita-Baylis-Hillman Carbonates

Yang Jingya^a, Li Nana^a, Zhou Hongyan^b, Li Tianyuan^a, Xie Dongtai^a, Li Zheng^a

a College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070;
b College of Science, Gansu Agricultural University, Lanzhou 730070

Received:2017-02-14 Revised:2017-03-24 Published:2017-04-13
Contact: 10.6023/cjoc201702015 E-mail:yangjy@nwnu.edu.cn
Supported by:
Project supported by the National Nature Science Foundation of China (Nos. 21362034, 21462038) and the Research Fund for the Doctoral Program of Higher Education of China (No. 20136203120005).

1. Selective S-Allylic Alkylation of 2-Thiopyrimidine with Morita-Baylis-Hillman Carbonates.PDF(2231KB)

Abstract

The S-allylic alkylation of 2-thiopyrimidine with Morita-Baylis-Hillman (MBH) carbonates catalyzed by 1,4-diazabicyclo[2.2.2]octane (DABCO) has been developed. A variety of Morita-Baylis-Hillman (MBH) carbonates reacted with 2-thiopyrimidine and gave the desired S-allylic alkylated products in 55%~99% yields with exclusive chemoselectivity and excellent regioselectivity. The mild reaction conditions, short reaction time, and broad substrate scope make this method very practical.

Key words: S-allylic alkylation, 2-thiopyrimidine, Morita-Baylis-Hillman (MBH) carbonates, allylic compounds, chemoselectivity, regioselectivity, heterocycles

Cite this article

Yang Jingya, Li Nana, Zhou Hongyan, Li Tianyuan, Xie Dongtai, Li Zheng. Selective S-Allylic Alkylation of 2-Thiopyrimidine with Morita-Baylis-Hillman Carbonates[J]. Chin. J. Org. Chem., 2017, 37(8): 2078-2085.

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2-巯基嘧啶与碳酸Morita-Baylis-Hillman酯的选择性S-烯丙基烷基化

Selective S-Allylic Alkylation of 2-Thiopyrimidine with Morita-Baylis-Hillman Carbonates

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