4]oxathiin-3-yl)methanols were synthesized via reactions of aryloxymethylthiiranes and N-bromosuccinimide (NBS) in DMSO under microwave irradiation. The reaction mechanism was proposed as an intramolecular aromatic electrophilic substitution of 1-bromo-2-(aryloxymethyl)thiiran-1-iums, generated from aryloxymethylthiiranes and NBS, and the subsequent DMSO nucleophilic ring opening reaction of thiiran-1-iums followed by
通过芳氧基甲基
硫烷和N-
溴琥珀
酰亚胺(
NBS)在
DMSO下微波辐射反应合成了(2,3-二氢苯并[ b ] [1,4]氧杂
嘧啶-3-基)
甲醇。该反应机理被认为是由芳氧基甲基
噻喃和
NBS生成的1-
溴-2-(芳氧基甲基)
噻喃-1-鎓的分子内芳族亲电取代,以及随后的
噻吩-1-鎓的
DMSO亲核开环反应,随后是排
水量。当前的方法提供了一种直接和简单的策略,可以从容易获得的芳氧基甲基
噻喃有效地制备(2,3-二氢苯并[ b ] [1,4]
氧杂蒽-3-基)
甲醇。