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 BBr 3. 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.
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