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Formation of N,S‐Containing Polycycles via Base Promoted Dimerization of N‐Phenacyl and N‐Benzylbenzothiazolium Bromides
ChemistrySelect ( IF 2.1 ) Pub Date : 2020-01-20 , DOI: 10.1002/slct.201904941
Bang‐Dong Ding 1 , Jing Sun 2 , Wang Jiang 2 , Gong Jin 2 , Chao‐Guo Yan 2
Affiliation  

The triethylamine promoted dimerization of N‐phenacylbenzothiazolium bromides in ethanol resulted in a mixture of N,O,S‐containing six fused‐cyclic compounds and N,S‐containing five fused‐cyclic compounds in moderate yields. On the other hand, the base promoted dimerization of N‐benzylbenzothiazolium bromides selectively afforded 2,3‐bis(4‐methylbenzyl)‐2,3‐dihydro‐2,2′‐bibenzo[d]thiazoles or 3,3′‐bis(4‐methoxybenzyl)‐2,2′‐spirobi[benzo[d]thiazoles] depending on the electronic effect of the substituents on the benzyl group. The plausible formation mechanisms of the various annulation products were rationally proposed.

中文翻译:

通过碱促进N-苯甲酰基和N-苄基苯并噻唑鎓溴化物的二聚形成含N,S的多环化合物

三乙胺促进了N-苯甲酰基苯并噻唑鎓溴化物在乙醇中的二聚,导致中等产量的N,O,S含六个稠合环化合物和N,S含五个稠合环化合物的混合物。另一方面,碱促进了N-苄基苯并噻唑溴化物的二聚反应,选择性地提供了2,3-双(4-甲基苄基)-2,3-二氢-2,2'-联苯并[ d ]噻唑或3,3'-bis (4-甲氧基苄基)-2,2'-螺双[苯并[ d ]噻唑]取决于苄基上取代基的电子效应。合理地提出了各种环状产物的合理形成机理。
更新日期:2020-01-21
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