Lewis 酸催化的丙烯醛二聚体和 1,3-二羰基化合物合成苯并呋喃和 4,5,6,7-四氢苯并呋喃。
Lewis Acid-Catalyzed Synthesis of Benzofurans and 4,5,6,7-Tetrahydrobenzofurans from Acrolein Dimer and 1,3-Dicarbonyl Compounds.
机构信息
Key Laboratory for Large-Format Battery Materials and System, Ministry of Education, School of Chemistry and Chemical Engineering , Huazhong University of Science and Technology , 430074 , Wuhan , China.
State Key Laboratory for Oxo Synthesis and Selective Oxidation , Lanzhou Institute of Chemical Physics , 730000 , Lanzhou , China.
出版信息
J Org Chem. 2019 Mar 1;84(5):2941-2950. doi: 10.1021/acs.joc.9b00270. Epub 2019 Feb 15.
2,3-Disubstituted benzofurans were synthesized from acrolein dimer and 1,3-dicarbonyl compounds by using N-bromosuccinimide as an oxidizing agent. The method was used to synthesize two commercial drug molecules, benzbromarone and amiodarone. The proposed mechanism of the reaction involves a N-bromosuccinimide (NBS)-assisted autotandem catalysis with Lewis acid catalyst. To proof the proposed mechanism, an intermediate was isolated successfully, which can be converted to 4,5,6,7-tetrahydrobenzofurans.
2,3-二取代苯并呋喃是由丙烯醛二聚体和 1,3-二羰基化合物通过使用 N-溴代丁二酰亚胺作为氧化剂合成的。该方法用于合成两种商业药物分子，苯溴马隆和胺碘酮。反应的提出的机制涉及 N-溴代丁二酰亚胺（NBS）辅助的自动串联催化与路易斯酸催化剂。为了证明提出的机制，成功分离出一种中间体，它可以转化为 4,5,6,7-四氢苯并呋喃。
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