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Short Paper | Regular issue | Vol 94, No. 1, 2017, pp.75-85
Published online, 5th December, 2016
DOI: 10.3987/COM-16-13586
Efficient and Diastereoselective Synthesis of bis-Quinazolinedione Derivatives via Low-Valent Titanium Reagent

Wei Lin,* Yazhen Wang, Yongxiang Zheng, and Daqing Shi*

*School of Chemistry and Environmental Engineering, Jiangsu Technology of University, Changzhou , Jiangsu 213001, China

Abstract

An efficient and simple method for the synthesis of chiral benzo[5,6][1,3]oxazino[4,3-c]quinoxaline-dione and octahydroquinoxalino- [1,2-c:4,3-c']diquinazoline-dione derivatives using 2-hydroxybenzaldehydes (or 2-nitrobenzaldehydes) and chiral cyclohexane-1,2-diamine as the starting materials promoted by low-valent titanium reagent has been described. The structures of all synthesized products were identified by their IR, 1H NMR, 13C NMR and HRMS analysis, and the structure of compound 8a was confirmed by X-ray diffraction analysis.