Regioselective bromination: Synthesis of brominated methoxyquinolines
Simple 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...
Ausführliche Beschreibung
Gespeichert in:
| Autor*in: |
Çakmak, Osman [verfasserIn] |
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| Format: |
E-Artikel |
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| Sprache: |
Englisch |
| Erschienen: |
2017transfer abstract |
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| Schlagwörter: |
Bromination of methoxy quinoline |
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| Umfang: |
8 |
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| Übergeordnetes Werk: |
Enthalten in: Therapeutic Advances in Pediatric Multiple Sclerosis - 2013, the international journal for the rapid publication of full original research papers and critical reviews in organic chemistry, Amsterdam [u.a.] |
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| Übergeordnetes Werk: |
volume:73 ; year:2017 ; number:36 ; day:7 ; month:09 ; pages:5389-5396 ; extent:8 |
| Links: |
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| DOI / URN: |
10.1016/j.tet.2017.07.044 |
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ELV035656751 |
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| 520 | |a Simple 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-8-methoxy-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 2,5-dibromoquinoline (24). This process selectively led to functionalization of the quinoline ring at both the C-2 and C-5 positions. | ||
| 520 | |a Simple 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-8-methoxy-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 2,5-dibromoquinoline (24). This process selectively led to functionalization of the quinoline ring at both the C-2 and C-5 positions. | ||
| 650 | 7 | |a Regioselective bromination |2 Elsevier | |
| 650 | 7 | |a Bromination of methoxy quinoline |2 Elsevier | |
| 650 | 7 | |a Quinoline |2 Elsevier | |
| 650 | 7 | |a Methoxy quinoline |2 Elsevier | |
| 650 | 7 | |a Multifunctionalization of quinoline |2 Elsevier | |
| 650 | 7 | |a Bromo quinoline |2 Elsevier | |
| 650 | 7 | |a 1,2,3,4-Tetrahydroquinoline |2 Elsevier | |
| 650 | 7 | |a Molecular bromine |2 Elsevier | |
| 700 | 1 | |a Ökten, Salih |4 oth | |
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10.1016/j.tet.2017.07.044 doi GBVA2017001000012.pica (DE-627)ELV035656751 (ELSEVIER)S0040-4020(17)30786-X DE-627 ger DE-627 rakwb eng 540 540 DE-600 610 VZ 150 VZ LING DE-30 fid 77.00 bkl Çakmak, Osman verfasserin aut Regioselective bromination: Synthesis of brominated methoxyquinolines 2017transfer abstract 8 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier Simple 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-8-methoxy-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 2,5-dibromoquinoline (24). This process selectively led to functionalization of the quinoline ring at both the C-2 and C-5 positions. Simple 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-8-methoxy-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 2,5-dibromoquinoline (24). This process selectively led to functionalization of the quinoline ring at both the C-2 and C-5 positions. Regioselective bromination Elsevier Bromination of methoxy quinoline Elsevier Quinoline Elsevier Methoxy quinoline Elsevier Multifunctionalization of quinoline Elsevier Bromo quinoline Elsevier 1,2,3,4-Tetrahydroquinoline Elsevier Molecular bromine Elsevier Ökten, Salih oth Enthalten in Elsevier Science Therapeutic Advances in Pediatric Multiple Sclerosis 2013 the international journal for the rapid publication of full original research papers and critical reviews in organic chemistry Amsterdam [u.a.] (DE-627)ELV011938943 volume:73 year:2017 number:36 day:7 month:09 pages:5389-5396 extent:8 https://doi.org/10.1016/j.tet.2017.07.044 Volltext GBV_USEFLAG_U GBV_ELV SYSFLAG_U FID-LING 77.00 Psychologie: Allgemeines VZ AR 73 2017 36 7 0907 5389-5396 8 045F 540 |
| spelling |
10.1016/j.tet.2017.07.044 doi GBVA2017001000012.pica (DE-627)ELV035656751 (ELSEVIER)S0040-4020(17)30786-X DE-627 ger DE-627 rakwb eng 540 540 DE-600 610 VZ 150 VZ LING DE-30 fid 77.00 bkl Çakmak, Osman verfasserin aut Regioselective bromination: Synthesis of brominated methoxyquinolines 2017transfer abstract 8 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier Simple 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-8-methoxy-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 2,5-dibromoquinoline (24). This process selectively led to functionalization of the quinoline ring at both the C-2 and C-5 positions. Simple 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-8-methoxy-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 2,5-dibromoquinoline (24). This process selectively led to functionalization of the quinoline ring at both the C-2 and C-5 positions. Regioselective bromination Elsevier Bromination of methoxy quinoline Elsevier Quinoline Elsevier Methoxy quinoline Elsevier Multifunctionalization of quinoline Elsevier Bromo quinoline Elsevier 1,2,3,4-Tetrahydroquinoline Elsevier Molecular bromine Elsevier Ökten, Salih oth Enthalten in Elsevier Science Therapeutic Advances in Pediatric Multiple Sclerosis 2013 the international journal for the rapid publication of full original research papers and critical reviews in organic chemistry Amsterdam [u.a.] (DE-627)ELV011938943 volume:73 year:2017 number:36 day:7 month:09 pages:5389-5396 extent:8 https://doi.org/10.1016/j.tet.2017.07.044 Volltext GBV_USEFLAG_U GBV_ELV SYSFLAG_U FID-LING 77.00 Psychologie: Allgemeines VZ AR 73 2017 36 7 0907 5389-5396 8 045F 540 |
| allfields_unstemmed |
10.1016/j.tet.2017.07.044 doi GBVA2017001000012.pica (DE-627)ELV035656751 (ELSEVIER)S0040-4020(17)30786-X DE-627 ger DE-627 rakwb eng 540 540 DE-600 610 VZ 150 VZ LING DE-30 fid 77.00 bkl Çakmak, Osman verfasserin aut Regioselective bromination: Synthesis of brominated methoxyquinolines 2017transfer abstract 8 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier Simple 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-8-methoxy-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 2,5-dibromoquinoline (24). This process selectively led to functionalization of the quinoline ring at both the C-2 and C-5 positions. Simple 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-8-methoxy-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 2,5-dibromoquinoline (24). This process selectively led to functionalization of the quinoline ring at both the C-2 and C-5 positions. Regioselective bromination Elsevier Bromination of methoxy quinoline Elsevier Quinoline Elsevier Methoxy quinoline Elsevier Multifunctionalization of quinoline Elsevier Bromo quinoline Elsevier 1,2,3,4-Tetrahydroquinoline Elsevier Molecular bromine Elsevier Ökten, Salih oth Enthalten in Elsevier Science Therapeutic Advances in Pediatric Multiple Sclerosis 2013 the international journal for the rapid publication of full original research papers and critical reviews in organic chemistry Amsterdam [u.a.] (DE-627)ELV011938943 volume:73 year:2017 number:36 day:7 month:09 pages:5389-5396 extent:8 https://doi.org/10.1016/j.tet.2017.07.044 Volltext GBV_USEFLAG_U GBV_ELV SYSFLAG_U FID-LING 77.00 Psychologie: Allgemeines VZ AR 73 2017 36 7 0907 5389-5396 8 045F 540 |
| allfieldsGer |
10.1016/j.tet.2017.07.044 doi GBVA2017001000012.pica (DE-627)ELV035656751 (ELSEVIER)S0040-4020(17)30786-X DE-627 ger DE-627 rakwb eng 540 540 DE-600 610 VZ 150 VZ LING DE-30 fid 77.00 bkl Çakmak, Osman verfasserin aut Regioselective bromination: Synthesis of brominated methoxyquinolines 2017transfer abstract 8 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier Simple 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-8-methoxy-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 2,5-dibromoquinoline (24). This process selectively led to functionalization of the quinoline ring at both the C-2 and C-5 positions. Simple 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-8-methoxy-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 2,5-dibromoquinoline (24). This process selectively led to functionalization of the quinoline ring at both the C-2 and C-5 positions. Regioselective bromination Elsevier Bromination of methoxy quinoline Elsevier Quinoline Elsevier Methoxy quinoline Elsevier Multifunctionalization of quinoline Elsevier Bromo quinoline Elsevier 1,2,3,4-Tetrahydroquinoline Elsevier Molecular bromine Elsevier Ökten, Salih oth Enthalten in Elsevier Science Therapeutic Advances in Pediatric Multiple Sclerosis 2013 the international journal for the rapid publication of full original research papers and critical reviews in organic chemistry Amsterdam [u.a.] (DE-627)ELV011938943 volume:73 year:2017 number:36 day:7 month:09 pages:5389-5396 extent:8 https://doi.org/10.1016/j.tet.2017.07.044 Volltext GBV_USEFLAG_U GBV_ELV SYSFLAG_U FID-LING 77.00 Psychologie: Allgemeines VZ AR 73 2017 36 7 0907 5389-5396 8 045F 540 |
| allfieldsSound |
10.1016/j.tet.2017.07.044 doi GBVA2017001000012.pica (DE-627)ELV035656751 (ELSEVIER)S0040-4020(17)30786-X DE-627 ger DE-627 rakwb eng 540 540 DE-600 610 VZ 150 VZ LING DE-30 fid 77.00 bkl Çakmak, Osman verfasserin aut Regioselective bromination: Synthesis of brominated methoxyquinolines 2017transfer abstract 8 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier Simple 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-8-methoxy-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 2,5-dibromoquinoline (24). This process selectively led to functionalization of the quinoline ring at both the C-2 and C-5 positions. Simple 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-8-methoxy-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 2,5-dibromoquinoline (24). This process selectively led to functionalization of the quinoline ring at both the C-2 and C-5 positions. Regioselective bromination Elsevier Bromination of methoxy quinoline Elsevier Quinoline Elsevier Methoxy quinoline Elsevier Multifunctionalization of quinoline Elsevier Bromo quinoline Elsevier 1,2,3,4-Tetrahydroquinoline Elsevier Molecular bromine Elsevier Ökten, Salih oth Enthalten in Elsevier Science Therapeutic Advances in Pediatric Multiple Sclerosis 2013 the international journal for the rapid publication of full original research papers and critical reviews in organic chemistry Amsterdam [u.a.] (DE-627)ELV011938943 volume:73 year:2017 number:36 day:7 month:09 pages:5389-5396 extent:8 https://doi.org/10.1016/j.tet.2017.07.044 Volltext GBV_USEFLAG_U GBV_ELV SYSFLAG_U FID-LING 77.00 Psychologie: Allgemeines VZ AR 73 2017 36 7 0907 5389-5396 8 045F 540 |
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Enthalten in Therapeutic Advances in Pediatric Multiple Sclerosis Amsterdam [u.a.] volume:73 year:2017 number:36 day:7 month:09 pages:5389-5396 extent:8 |
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Regioselective bromination Bromination of methoxy quinoline Quinoline Methoxy quinoline Multifunctionalization of quinoline Bromo quinoline 1,2,3,4-Tetrahydroquinoline Molecular bromine |
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regioselective bromination: synthesis of brominated methoxyquinolines |
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Regioselective bromination: Synthesis of brominated methoxyquinolines |
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Simple 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-8-methoxy-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 2,5-dibromoquinoline (24). This process selectively led to functionalization of the quinoline ring at both the C-2 and C-5 positions. |
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Simple 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-8-methoxy-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 2,5-dibromoquinoline (24). This process selectively led to functionalization of the quinoline ring at both the C-2 and C-5 positions. |
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Simple 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-8-methoxy-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 2,5-dibromoquinoline (24). This process selectively led to functionalization of the quinoline ring at both the C-2 and C-5 positions. |
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