Chinese Journal of Organic Chemistry >
Efficient and Stereoselective Synthesis of the Chiral Dihydroxy-bisquinazoline-dione Derivatives and Their Application in Asymmetric Catalysis
Received date: 2017-01-22
Revised date: 2017-03-14
Online published: 2017-04-10
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).
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
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]. Chinese Journal of Organic Chemistry, 2017 , 37(8) : 2094 -2100 . DOI: 10.6023/cjoc201701044
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