化学
区域选择性
迈克尔反应
硫醚
分子内力
戒指(化学)
废止
串联
噻唑
立体化学
芳基
药物化学
组合化学
催化作用
有机化学
材料科学
烷基
复合材料
作者
Jyoti M. Honnanayakanavar,Battu Harish,Jagadeesh Babu Nanubolu,Surisetti Suresh
标识
DOI:10.1021/acs.joc.0c00275
摘要
A copper-catalyzed tandem process integrating regioselective N-arylation, followed by aza-Michael addition, is disclosed using 2-aminobenzothiazoles and ortho-halo cinnamic acid congeners. This process generated diverse tetracyclic 5H-benzothiazolo[3,2-a]quinazoline derivatives in moderate to good yields. The present tandem reaction appears to proceed through concomitant ring opening of 2-aminobenzothiazole and S-arylation to give the ortho-cyanamide-substituted diaryl thioether intermediate. The thus generated intermediate likely undergoes an unprecedented Truce–Smiles-type rearrangement involving S- to N-aryl migration, followed by reformation of the thiazole ring and intramolecular aza-Michael addition to furnish the title products.
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