通过1,2-环亚磺酰胺合成对映体纯的1,4-苯并恶嗪。左氧氟沙星的合成。
Enantiopure 1,4-benzoxazines via 1,2-cyclic sulfamidates. Synthesis of levofloxacin.
作者信息
Bower John F, Szeto Peter, Gallagher Timothy
机构信息
School of Chemistry, University of Bristol, Bristol BS8 1TS, U.K.
出版信息
Org Lett. 2007 Aug 16;9(17):3283-6. doi: 10.1021/ol0712475. Epub 2007 Jul 28.
1,2-Cyclic sulfamidates undergo efficient and regiospecific nucleophilic cleavage with 2-bromophenols (and related anilines and thiophenols), followed by Pd(0)-mediated amination to provide an entry to substituted and enantiomerically pure 1,4-benzoxazines (and quinoxalines and 1,4-benzothiazines). This chemistry provides a short and efficient entry to (3S)-3-methyl-1,4-benzoxazine 19, a late stage intermediate in the synthesis of levofloxacin.
1,2-环氨基磺酸酯与2-溴苯酚（以及相关的苯胺和硫酚）发生高效且区域选择性的亲核裂解，随后经钯(0)介导的胺化反应，可用于制备取代的对映体纯的1,4-苯并恶嗪（以及喹喔啉和1,4-苯并噻嗪）。该化学方法为合成左氧氟沙星后期中间体(3S)-3-甲基-1,4-苯并恶嗪19提供了一条简短而高效的途径。
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