Acidic rearrangement of benzyl group in flavone benzyl ethers and its regioselectivity

注册 English

Acidic rearrangement of benzyl group in flavone benzyl ethers and its regioselectivity

Chong-Qing Wang , Xin Chen , Jun-Hang Jiang , Hui Tang , Kong-Kai Zhu , You-Jun Zhou , Can-Hui Zheng , Ju Zhu

Citation: Chong-Qing Wang, Xin Chen, Jun-Hang Jiang, Hui Tang, Kong-Kai Zhu, You-Jun Zhou, Can-Hui Zheng, Ju Zhu. Acidic rearrangement of benzyl group in flavone benzyl ethers and its regioselectivity[J]. Chinese Chemical Letters, 2015, 26(6): 793-796. doi: 10.1016/j.cclet.2015.03.035 shu

shu

Acidic rearrangement of benzyl group in flavone benzyl ethers and its regioselectivity

Chong-Qing Wang ^a, ,
Xin Chen ^b, ,
Jun-Hang Jiang ^a, ,
Hui Tang ^c, ,
Kong-Kai Zhu ^d, ,
You-Jun Zhou ^{a,
,} ,
Can-Hui Zheng ^{a,
,} ,
Ju Zhu ^{a,
,}

通讯作者: You-Jun Zhou,
Can-Hui Zheng,
Ju Zhu,

基金项目:

Shanghai Natural Science Foundation (No. 09ZR1438800) (No. 09ZR1438800)

Shanghai Education Development Foundation (12CG42). (12CG42)

摘要: The benzyl-substituted flavone compounds are rare in nature, while some of which have interesting biological activities. The total synthesis of benzyl-substituted flavone derivatives via the acidic rearrangement of benzyl groups in flavone benzyl ethers, and the complicated regioselectivity of the rearrangement were reported. The regioselectivity was proposed to be determined by the steric hindrance as well as the ease of electrophilic substitution reaction for benzyl cations at different positions of corresponding debenzylated flavone compounds.

关键词:

English

Acidic rearrangement of benzyl group in flavone benzyl ethers and its regioselectivity

Chong-Qing Wang ^a, ,
Xin Chen ^b, ,
Jun-Hang Jiang ^a, ,
Hui Tang ^c, ,
Kong-Kai Zhu ^d, ,
You-Jun Zhou ^{a,
,} ,
Can-Hui Zheng ^{a,
,} ,
Ju Zhu ^{a,
,}

1.
a School of Pharmacy, Second Military Medical University, Shanghai 200433, China;
2.
b School of Biology and Pharmaceutical Engineering, Wuhan Polytechnic University, Wuhan 430023, China;
3.
c Pharmacy, Provincial Hospital Affiliated to Shandong University, Jinan 250021, China;
4.
d State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China

Corresponding author: You-Jun Zhou, Can-Hui Zheng, Ju Zhu,

Received Date: 21 January 2015
Available Online: 02 April 2015
Fund Project:

Abstract: The benzyl-substituted flavone compounds are rare in nature, while some of which have interesting biological activities. The total synthesis of benzyl-substituted flavone derivatives via the acidic rearrangement of benzyl groups in flavone benzyl ethers, and the complicated regioselectivity of the rearrangement were reported. The regioselectivity was proposed to be determined by the steric hindrance as well as the ease of electrophilic substitution reaction for benzyl cations at different positions of corresponding debenzylated flavone compounds.

Key words:

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