扩展恶唑的合成 III：2-（苯磺酰基）甲基-4,5-二芳基恶唑的反应。

Synthesis of Extended Oxazoles III: Reactions of 2-(Phenylsulfonyl)methyl-4,5-diaryloxazoles.

机构信息

Department of Chemistry, University of Louisville , 2320 South Brook Street, Louisville, Kentucky 40292, United States.

出版信息

J Org Chem. 2016 Nov 4;81(21):10521-10526. doi: 10.1021/acs.joc.6b01280. Epub 2016 Aug 4.

DOI:10.1021/acs.joc.6b01280

Abstract

2-((Phenylsulfonyl)methyl)-4,5-diphenyloxazole is a useful scaffold for synthetic elaboration at the 2-methylene position thereby affording extended oxazoles. The corresponding α-sulfonyl anion reacts smoothly with diverse alkyl halides giving monoalkylated (47-90%), dialkylated (50-97%), and cyclic (59-93%) products. The reductive desulfonylation of the monoalkylated and selected dialkylated products was optimized with a magnesium/mercuric chloride reagent system and afforded desulfonylated products in the range of 66-97%. The anti-inflammatory Oxaprozin was prepared using the α-sulfonyl carbanion strategy along with optimized desulfonylation.

摘要

2-((苯磺酰基)甲基)-4,5-二苯基恶唑是在 2-亚甲基位置进行合成修饰的有用支架，从而得到扩展的恶唑。相应的α-磺酰基阴离子与各种卤代烃反应顺利，得到单烷基化（47-90%）、二烷基化（50-97%）和环状（59-93%）产物。用镁/氯化汞试剂体系对单烷基化和选定的二烷基化产物进行了最佳的还原脱磺酰基反应，得到脱磺酰基产物的范围为 66-97%。采用α-磺酰基碳负离子策略并优化脱磺酰基反应，制备了抗炎药奥沙普秦。