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Chinese Journal of Organic Chemistry >

2017 , Vol. 37 >Issue 8: 2078 - 2085

DOI: https://doi.org/10.6023/cjoc201702015

ARTICLE

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

  • Yang Jingya ,
  • Li Nana ,
  • Zhou Hongyan ,
  • Li Tianyuan ,
  • Xie Dongtai ,
  • Li Zheng
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  • a College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070;
    b College of Science, Gansu Agricultural University, Lanzhou 730070

Received date: 2017-02-14

  Revised date: 2017-03-24

  Online published: 2017-04-13

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).

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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]. Chinese Journal of Organic Chemistry, 2017 , 37(8) : 2078 -2085 . DOI: 10.6023/cjoc201702015

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