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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.", "publication_date": "2017-01-01", "resource_type": { "id": "publication-article", "title": { "en": "Journal article", "tr": "Dergi makalesi" } }, "rights": [ { "description": { "en": "The Creative Commons Attribution license allows re-distribution and re-use of a licensed work on the condition that the creator is appropriately credited." }, "icon": "cc-by-icon", "id": "cc-by-4.0", "props": { "scheme": "spdx", "url": "https://creativecommons.org/licenses/by/4.0/legalcode" }, "title": { "en": "Creative Commons Attribution 4.0 International" } } ], "title": "Regioselective bromination: Synthesis of brominated methoxyquinolines" }, "parent": { "access": { "owned_by": { "user": "1" } }, "communities": { "default": "be1a9c54-8a57-4004-beac-45f642d1fb86", "entries": [ { "access": { "member_policy": "open", "members_visibility": "public", "record_submission_policy": "open", "review_policy": "open", "visibility": "public" }, "children": { "allow": false }, "created": "2021-03-15T05:37:50.780180+00:00", "deletion_status": { "is_deleted": false, "status": "P" }, "id": "be1a9c54-8a57-4004-beac-45f642d1fb86", "links": {}, "metadata": { "curation_policy": "", "description": "", "page": "", "title": "TUBITAK Destekli Projelerden \u00c7\u0131kan Yay\u0131nlar Toplulu\u011fu " }, "revision_id": 0, "slug": "tubitak-destekli-proje-yayinlari", "updated": "2021-11-26T15:43:54.504251+00:00" } ], "ids": [ "be1a9c54-8a57-4004-beac-45f642d1fb86" ] }, "id": "49994", "pids": {} }, "pids": { "doi": { "identifier": "10.1016/j.tet.2017.07.044", "provider": "external" }, "oai": { "identifier": "oai:zenodo.org:49995", "provider": "oai" } }, "revision_id": 1, "stats": { "all_versions": { "data_volume": 2926.0, "downloads": 22, "unique_downloads": 22, "unique_views": 75, "views": 75 }, "this_version": { "data_volume": 2926.0, "downloads": 22, "unique_downloads": 22, "unique_views": 75, "views": 75 } }, "status": "published", "swh": {}, "updated": "2021-03-15T22:36:54.449033+00:00", "versions": { "index": 1, "is_latest": true } }