Base-Induced Cyclisation of ortho -Substituted 2-Phenyloxazolines to Give 3-Aminobenzofurans and Related Heterocycles
Base-Induced Cyclisation of ortho -Substituted 2-Phenyloxazolines to Give 3-Aminobenzofurans and Related Heterocycles
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DOI：
10.1055/s-0036-1588503
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发表时间：
2017-09-01
期刊：
影响因子：
2
通讯作者：
Slawin, Alexandra M. Z.
中科院分区：
文献类型：
--
作者：
Aitken, R. Alan;Harper, Andrew D.;Slawin, Alexandra M. Z.
用丁基锂和叔丁醇钾处理邻苄氧基苯基恶唑啉，导致恶唑啉开环环化，得到2-芳基-3-氨基苯并呋喃。与相应的苄硫基和苄氨基化合物也发生反应，分别得到苯并噻吩和吲哚。使用邻-烯丙氧基苯基恶唑啉得到相应的2-乙烯基苯并呋喃，而α-甲基苄氧基和苄基磺酰基化合物均形成稳定的螺恶唑烷产物。测定了一种氨基苯并噻吩产物的X射线结构。
Treatment of ortho-benzyloxyphenyloxazolines with butyllithium and potassium tert-butoxide results in cyclisation with ring opening of the oxazoline to give 2-aryl-3-aminobenzofurans. The reaction also occurs with the corresponding benzylthio and benzylamino compounds to give benzothiophenes and indoles, respectively. Use of an ortho-allyloxyphenyloxazoline gives the corresponding 2-vinylbenzofuran, while both alpha-methylbenzyloxy and benzylsulfonyl compounds form stable spirooxazolidine products. The X-ray structure of an amino-benzothiophene product has been determined.