Efficient and Stereoselective Synthesis of the Chiral Dihydroxy-bisquinazoline-dione Derivatives and Their Application in Asymmetric Catalysis

doi:10.6023/cjoc201701044

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (8): 2094-2100.DOI: 10.6023/cjoc201701044 Previous Articles Next Articles

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手性双苯并噁嗪-2-酮二酚衍生物的高效合成及其在不对称催化中的应用

林伟^a, 蔡琦^a, 郑纯智^a, 黄志斌^b, 史达清^b

a 江苏理工学院化学与环境工程学院常州 213001;
b 苏州大学材料与化学化工学部苏州 215123

收稿日期:2017-01-22 修回日期:2017-03-14 发布日期:2017-04-10
通讯作者: 林伟, 史达清 E-mail:linwei@jsut.edu.cn;dqshi@suda.edu.cn
基金资助:
国家自然科学基金（No.21502074）和江苏省高校自然科学重大研究（No.15KJA150006）资助项目.

Efficient and Stereoselective Synthesis of the Chiral Dihydroxy-bisquinazoline-dione Derivatives and Their Application in Asymmetric Catalysis

Lin Wei^a, Cai Qi^a, Zheng Chunzhi^a, Huang Zhibin^b, Shi Daqing^b

a School of Chemistry and Environmental Engineering, Jiangsu Technology of University, Changzhou 213001;
b College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123

Received:2017-01-22 Revised:2017-03-14 Published:2017-04-10
Contact: 10.6023/cjoc201701044 E-mail:linwei@jsut.edu.cn;dqshi@suda.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21502074) and the Major Basic Research Project of the Natural Science Foundation of the Jiangsu Higher Education Institutions (No. 15KJA150006).

1. Efficient and Stereoselective Synthesis of the Chiral Dihydroxy-bisquinazoline-dione Derivatives and Their Application in Asymmetric Catalysis.PDF(8477KB)

Abstract

An efficient and simple method for the synthesis of chiral benzo[5,6][1,3]oxazino[4,3-c]quinoxaline-dione is reported. 2-Hydroxybenzaldehydes and diamines were utilized as the starting materials, the formed diimines then underwent a reductive-cyclization process with triphosgene to give bis-quinazoline-dione derivatives induced by low-valent titanium reagent. Then through the conversion of functional groups, the bis-quinazoline-dione compounds containing hydroxy group have been obtained from their corresponding compounds containing methoxy group in the presence of BBr₃. In addition, the dihydroxy-bis-quinazoline-dione derivatives were applied on the asymmetric nucleophilic addition of Et₂Zn to aldehydes. The reported method is the efficient approach for the synthesis of dihydroxy-bis-quinazoline-dione derivatives.

Key words: bis-quinazoline-dione, asymmetric, synthesis

Cite this article

Lin Wei, Cai Qi, Zheng Chunzhi, Huang Zhibin, Shi Daqing. Efficient and Stereoselective Synthesis of the Chiral Dihydroxy-bisquinazoline-dione Derivatives and Their Application in Asymmetric Catalysis[J]. Chin. J. Org. Chem., 2017, 37(8): 2094-2100.

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手性双苯并噁嗪-2-酮二酚衍生物的高效合成及其在不对称催化中的应用

Efficient and Stereoselective Synthesis of the Chiral Dihydroxy-bisquinazoline-dione Derivatives and Their Application in Asymmetric Catalysis

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