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Tandem Copper-Catalyzed Regioselective N-Arylation-Aza-Michael Addition: Synthesis of Tetracyclic 5H-Benzothiazolo[3,2-a]quinazoline Derivatives.
The Journal of Organic Chemistry ( IF 3.6 ) Pub Date : 2020-06-30 , DOI: 10.1021/acs.joc.0c00275 Jyoti M Honnanayakanavar 1, 2 , Battu Harish 1, 2 , Jagadeesh Babu Nanubolu 3 , Surisetti Suresh 1, 2
The Journal of Organic Chemistry ( IF 3.6 ) Pub Date : 2020-06-30 , DOI: 10.1021/acs.joc.0c00275 Jyoti M Honnanayakanavar 1, 2 , Battu Harish 1, 2 , Jagadeesh Babu Nanubolu 3 , Surisetti Suresh 1, 2
Affiliation
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.
中文翻译:
串联铜催化的区域选择性N-芳基化-Aza-Michael加成反应:四环5H-苯并噻唑并[3,2-a]喹唑啉衍生物的合成。
公开了使用2-氨基苯并噻唑和邻卤代肉桂酸同类物的铜催化的串联方法,其结合区域选择性的N-芳基化,然后进行氮杂-迈克尔加成。该过程以中等至良好的产率产生了多种多样的四环5 H-苯并噻唑并[3,2- a ]喹唑啉衍生物。当前的串联反应似乎是通过2-氨基苯并噻唑的同时开环和S-芳基化而进行的,得到邻-氰酰胺取代的二芳基硫醚中间体。这样生成的中间体可能经历了前所未有的Truce-Smiles型重排,涉及S-到N-芳基迁移,然后重新形成噻唑环和分子内氮杂-Michael加成物,得到标题产物。
更新日期:2020-07-17
中文翻译:
串联铜催化的区域选择性N-芳基化-Aza-Michael加成反应:四环5H-苯并噻唑并[3,2-a]喹唑啉衍生物的合成。
公开了使用2-氨基苯并噻唑和邻卤代肉桂酸同类物的铜催化的串联方法,其结合区域选择性的N-芳基化,然后进行氮杂-迈克尔加成。该过程以中等至良好的产率产生了多种多样的四环5 H-苯并噻唑并[3,2- a ]喹唑啉衍生物。当前的串联反应似乎是通过2-氨基苯并噻唑的同时开环和S-芳基化而进行的,得到邻-氰酰胺取代的二芳基硫醚中间体。这样生成的中间体可能经历了前所未有的Truce-Smiles型重排,涉及S-到N-芳基迁移,然后重新形成噻唑环和分子内氮杂-Michael加成物,得到标题产物。