Parallel synthesis of oxazolines and thiazolines by tandem condensation-cyclodehydration of carboxylic acids with amino alcohols and aminothiols.
Parallel synthesis of oxazolines and thiazolines by tandem condensation-cyclodehydration of carboxylic acids with amino alcohols and aminothiols.
复制标题
通过羧酸与氨基醇和氨基硫醇的串联缩合环脱水并联合成恶唑啉和噻唑啉。
DOI：
10.1021/cc020041m
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发表时间：
2002
影响因子：
--
通讯作者：
Wang,Xiaodong
中科院分区：
文献类型：
--
作者：
Wipf,Peter;Wang,Xiaodong
使用新开发的方法，以中等至优异的产率合成了恶唑啉和噻唑啉的组合库。在3-硝基苯硼酸作为脱水催化剂的存在下，游离羧酸与氨基醇和氨基硫醇直接缩合。库合成说明了该过程的范围： 经过传统反应优化后，在 Radleys GreenHouse 并行合成器的 24 反应装置中成功制备了总共 17 种恶唑啉和 6 种噻唑啉。平行反应的产率从中等到优异不等，很大程度上取决于羧酸酯的反应性和官能化，并且通常超过传统反应装置的产率。将反应混合物通过短 PrepSep SPE Florisil 柱后，以高纯度分离出目标化合物（根据 GC 分析，平均纯度为 96%）。
A combinatorial library of oxazolines and thiazolines was synthesized in moderate to excellent yields using a newly developed methodology. Free carboxylic acids were directly condensed with amino alcohols and aminothiols in the presence of 3-nitrophenylboronic acid as a dehydration catalyst. The library synthesis illustrates the scope of this process: After traditional reaction optimization, a total of 17 oxazolines and 6 thiazolines were successfully prepared in a 24-reaction setup in a Radleys GreenHouse parallel synthesizer. The yields of the parallel reactions ranged from moderate to excellent, depending largely on carboxylate reactivity and functionalization, and generally exceeded those of the traditional reaction setup. The target compounds were isolated in high purities (average purity is 96% according to GC analysis) after passing reaction mixtures through short PrepSep SPE Florisil cartridges.