通过芳基甲基叠氮化物的酸促进重排实现3-溴喹啉衍生物的区域选择性合成及四氢喹啉的非对映选择性合成。

Regioselective Synthesis of 3-Bromoquinoline Derivatives and Diastereoselective Synthesis of Tetrahydroquinolines via Acid-Promoted Rearrangement of Arylmethyl Azides.

作者信息

Tummatorn Jumreang, Poonsilp Piyapratch, Nimnual Phongprapan, Janprasit Jindaporn, Thongsornkleeb Charnsak, Ruchirawat Somsak

机构信息

†Laboratory of Medicinal Chemistry, Chulabhorn Research Institute, 54 Kamphaeng Phet 6, Laksi, Bangkok 10210, Thailand.

‡Program on Chemical Biology, Chulabhorn Graduate Institute, Center of Excellence on Environmental Health and Toxicology (EHT), Ministry of Education, 54 Kamphaeng Phet 6, Laksi, Bangkok 10210, Thailand.

出版信息

J Org Chem. 2015 May 1;80(9):4516-25. doi: 10.1021/acs.joc.5b00375. Epub 2015 Apr 22.

DOI:10.1021/acs.joc.5b00375

PMID:25876191

Abstract

Regioselective synthesis of 3-bromoquinoline derivatives was achieved via a formal [4 + 2]-cycloaddition between N-aryliminium ion, generated from arylmethyl azides, and 1-bromoalkynes. This method could also be applied to other quinoline derivatives using appropriate alkynes. Moreover, the current strategy could be utilized for the diastereoselective synthesis of tetrahydroquinoline derivatives employing alkenyl substrates in good to excellent yields.

摘要

通过由芳基甲基叠氮化物生成的N-芳基亚胺离子与1-溴代炔烃之间的形式上的[4 + 2]环加成反应，实现了3-溴喹啉衍生物的区域选择性合成。使用适当的炔烃，该方法也可应用于其他喹啉衍生物。此外，当前策略可用于利用烯基底物以良好至优异的产率非对映选择性合成四氢喹啉衍生物。