Wang Shu-Liang, Zhang Ge, Jie Ding, Jiang Bo, Wang Xing-Han, Tu Shu-Jiang
School of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Xuzhou Normal University, Xuzhou, P.R. China.
Comb Chem High Throughput Screen. 2012 Jun 1;15(5):400-10. doi: 10.2174/138620712800194459.
A new multicomponent domino reaction for rapid and regioselective synthesis of highly functionalized benzo[h]naphtho[2,3-a]acridine-15,16(5H,14H)-diones has been established. The reaction can be conducted by using readily available and inexpensive substrates under microwave irradiation. The procedures are facile, avoiding timeconsuming and costly syntheses, tedious work-up and purifications of precursors as well as protection/deprotection of functional groups. This method is much more efficient due to short reaction times and easy work up. The resulting naphthoacridines have been readily converted into benzoquinoxaline-fused benzoquinoline analogues by treating with benzene-1,2-diamine under microwave irradiation. The structural assignment has been ambiguously confirmed by X-ray analysis. A new mechanism has been proposed for this new multicomponent domino process.
已建立了一种用于快速、区域选择性合成高度官能化苯并[h]萘并[2,3-a]吖啶-15,16(5H,14H)-二酮的新型多组分多米诺反应。该反应可在微波辐射下使用容易获得且廉价的底物进行。该方法简便,避免了耗时且昂贵的合成、繁琐的后处理和前体的纯化以及官能团的保护/脱保护。由于反应时间短且后处理容易,该方法效率更高。通过在微波辐射下用苯-1,2-二胺处理,所得的萘并吖啶已很容易地转化为苯并喹喔啉稠合的苯并喹啉类似物。通过X射线分析对结构归属进行了明确确认。已为这种新型多组分多米诺过程提出了一种新机制。