Çakmak, OsmanÖkten, Salih2020-06-252020-06-252017closedAccess0040-4020https://doi.org/10.1016/j.tet.2017.07.044https://hdl.handle.net/20.500.12587/6876Okten, Salih/0000-0001-9656-1803Simple synthetic methods are described for the synthesis of valuable polyfunctional brominated methoxyquinolines 10-13, 20-21, and 24-25. Three regioselective routes are described for convenient preparation of brominated methoxyquinolines at the C-2, C-3, and C-5 positions with consecutive reaction steps under mild reaction conditions using molecular bromine. While bromination of 6-bromo-8methoxy-1,2,3,4-tetrahydroquinoline (8) selectively gave 3,6-dibromo-8-methoxyquinoline (10) and 3,5,6-tribromo-8-methoxyquinoline (11), the reaction of 6,8-dimethoxy-1,2,3,4-tetrahydroquinoline (9) resulted in the formation of 3-bromo-6,8-dimethoxyqinoline (12) and tribromide 13. On the other hand, direct bromination of 6-methoxy- 17 and 6,8-dimethoxyquinoline (19) gave 5-bromo derivatives 20 and 21. However, the reaction 3,6-dimethoxyquinoline (8) resulted in dibromination to form 2,5dibromoquinoline (24). This process selectively led to functionalization of the quinoline ring at both the C-2 and C-5 positions. (C)2017 Elsevier Ltd. All rights reserved.eninfo:eu-repo/semantics/closedAccessQuinoline1,2,3,4-TetrahydroquinolineBromo quinolineMethoxy quinolineBromination of methoxy quinolineMultifunctionalization of quinolineRegioselective brominationMolecular bromineArticle73365389539610.1016/j.tet.2017.07.0442-s2.0-85026428774Q3WOS:000408179400008Q2