Synthesis of 2,2-difluoro-2-arylethylamines as fluorinated analogs of octopamine and noradrenaline
A series of 2,2-difluoro-2-arylethylamines was synthesized as fluorinated analogs of octopamine and noradrenaline with the expectation of bioisosteric OH/F exchanges. The syntheses of these compounds were performed by a Suzuki–Miyaura cross-coupling reaction of 4-(bromodifluoroacetyl)morpholine with...
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| Format: | Article |
| Language: | English |
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De Gruyter
2022-03-01
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| Series: | Heterocyclic Communications |
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| Online Access: | https://doi.org/10.1515/hc-2022-0005 |
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| author | Tarui Atsushi Kamata Erika Ebisu Koji Kawai Yui Araki Ryota Yabe Takeshi Karuo Yukiko Sato Kazuyuki Kawai Kentaro Omote Masaaki |
| author_facet | Tarui Atsushi Kamata Erika Ebisu Koji Kawai Yui Araki Ryota Yabe Takeshi Karuo Yukiko Sato Kazuyuki Kawai Kentaro Omote Masaaki |
| author_sort | Tarui Atsushi |
| collection | DOAJ |
| description | A series of 2,2-difluoro-2-arylethylamines was synthesized as fluorinated analogs of octopamine and noradrenaline with the expectation of bioisosteric OH/F exchanges. The syntheses of these compounds were performed by a Suzuki–Miyaura cross-coupling reaction of 4-(bromodifluoroacetyl)morpholine with aryl boronic acids to produce the intermediate 2,2-difluoro-2-arylacetamides, followed by transformation of difluoroacetamide to difluoroethylamine. |
| first_indexed | 2024-04-11T14:03:01Z |
| format | Article |
| id | doaj.art-c50cd797b45646938a2a6810485c5bfa |
| institution | Directory Open Access Journal |
| issn | 2191-0197 |
| language | English |
| last_indexed | 2024-04-11T14:03:01Z |
| publishDate | 2022-03-01 |
| publisher | De Gruyter |
| record_format | Article |
| series | Heterocyclic Communications |
| spelling | doaj.art-c50cd797b45646938a2a6810485c5bfa2022-12-22T04:20:01ZengDe GruyterHeterocyclic Communications2191-01972022-03-01281263410.1515/hc-2022-0005Synthesis of 2,2-difluoro-2-arylethylamines as fluorinated analogs of octopamine and noradrenalineTarui Atsushi0Kamata Erika1Ebisu Koji2Kawai Yui3Araki Ryota4Yabe Takeshi5Karuo Yukiko6Sato Kazuyuki7Kawai Kentaro8Omote Masaaki9Faculty of Pharmaceutical Sciences, Setsunan University, 45-1, Nagaotoge-cho, Hirakata, Osaka 573-0101, JapanFaculty of Pharmaceutical Sciences, Setsunan University, 45-1, Nagaotoge-cho, Hirakata, Osaka 573-0101, JapanFaculty of Pharmaceutical Sciences, Setsunan University, 45-1, Nagaotoge-cho, Hirakata, Osaka 573-0101, JapanFaculty of Pharmaceutical Sciences, Setsunan University, 45-1, Nagaotoge-cho, Hirakata, Osaka 573-0101, JapanFaculty of Pharmaceutical Sciences, Setsunan University, 45-1, Nagaotoge-cho, Hirakata, Osaka 573-0101, JapanFaculty of Pharmaceutical Sciences, Setsunan University, 45-1, Nagaotoge-cho, Hirakata, Osaka 573-0101, JapanFaculty of Pharmaceutical Sciences, Setsunan University, 45-1, Nagaotoge-cho, Hirakata, Osaka 573-0101, JapanFaculty of Pharmaceutical Sciences, Setsunan University, 45-1, Nagaotoge-cho, Hirakata, Osaka 573-0101, JapanFaculty of Pharmaceutical Sciences, Setsunan University, 45-1, Nagaotoge-cho, Hirakata, Osaka 573-0101, JapanFaculty of Pharmaceutical Sciences, Setsunan University, 45-1, Nagaotoge-cho, Hirakata, Osaka 573-0101, JapanA series of 2,2-difluoro-2-arylethylamines was synthesized as fluorinated analogs of octopamine and noradrenaline with the expectation of bioisosteric OH/F exchanges. The syntheses of these compounds were performed by a Suzuki–Miyaura cross-coupling reaction of 4-(bromodifluoroacetyl)morpholine with aryl boronic acids to produce the intermediate 2,2-difluoro-2-arylacetamides, followed by transformation of difluoroacetamide to difluoroethylamine.https://doi.org/10.1515/hc-2022-0005difluoroacetamidefluorine analoguesuzuki–miyaura couplingoctopaminenoradrenaline |
| spellingShingle | Tarui Atsushi Kamata Erika Ebisu Koji Kawai Yui Araki Ryota Yabe Takeshi Karuo Yukiko Sato Kazuyuki Kawai Kentaro Omote Masaaki Synthesis of 2,2-difluoro-2-arylethylamines as fluorinated analogs of octopamine and noradrenaline Heterocyclic Communications difluoroacetamide fluorine analogue suzuki–miyaura coupling octopamine noradrenaline |
| title | Synthesis of 2,2-difluoro-2-arylethylamines as fluorinated analogs of octopamine and noradrenaline |
| title_full | Synthesis of 2,2-difluoro-2-arylethylamines as fluorinated analogs of octopamine and noradrenaline |
| title_fullStr | Synthesis of 2,2-difluoro-2-arylethylamines as fluorinated analogs of octopamine and noradrenaline |
| title_full_unstemmed | Synthesis of 2,2-difluoro-2-arylethylamines as fluorinated analogs of octopamine and noradrenaline |
| title_short | Synthesis of 2,2-difluoro-2-arylethylamines as fluorinated analogs of octopamine and noradrenaline |
| title_sort | synthesis of 2 2 difluoro 2 arylethylamines as fluorinated analogs of octopamine and noradrenaline |
| topic | difluoroacetamide fluorine analogue suzuki–miyaura coupling octopamine noradrenaline |
| url | https://doi.org/10.1515/hc-2022-0005 |
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