Highly Selective Synthesis of 6-Glyoxylamidoquinoline Derivatives via Palladium-Catalyzed Aminocarbonylation
The aminocarbonylation of 6-iodoquinoline has been investigated in the presence of large series of amine nucleophiles, providing an efficient synthetic route for producing various quinoline-6-carboxamide and quinoline-6-glyoxylamide derivatives. It was shown, after detailed optimization study, that...
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MDPI AG
2021-12-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/1/4 |
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| author | Sami Chniti László Kollár Attila Bényei Attila Takács |
| author_facet | Sami Chniti László Kollár Attila Bényei Attila Takács |
| author_sort | Sami Chniti |
| collection | DOAJ |
| description | The aminocarbonylation of 6-iodoquinoline has been investigated in the presence of large series of amine nucleophiles, providing an efficient synthetic route for producing various quinoline-6-carboxamide and quinoline-6-glyoxylamide derivatives. It was shown, after detailed optimization study, that the formation of amides and ketoamides is strongly influenced by the reaction conditions. Performing the reactions at 40 bar of carbon monoxide pressure in the presence of Pd(OAc)<sub>2</sub>/2 PPh<sub>3</sub>, the corresponding 2-ketocarboxamides were formed as major products (up to 63%). When the monodentate triphenylphosphine was replaced by the bidentate XantPhos, the quinoline-6-carboxamide derivatives were synthesized almost exclusively under atmospheric conditions (up to 98%). The isolation and characterization of the new carbonylated products of various structures were also accomplished. Furthermore, the structure of three new mono- and double-carbonylated compounds were unambiguously established by using a single-crystal XRD study. |
| first_indexed | 2024-03-10T03:31:39Z |
| format | Article |
| id | doaj.art-2ce41458b6804a2c81c57f144fd1dd3a |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T03:31:39Z |
| publishDate | 2021-12-01 |
| publisher | MDPI AG |
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| series | Molecules |
| spelling | doaj.art-2ce41458b6804a2c81c57f144fd1dd3a2023-11-23T11:55:11ZengMDPI AGMolecules1420-30492021-12-01271410.3390/molecules27010004Highly Selective Synthesis of 6-Glyoxylamidoquinoline Derivatives via Palladium-Catalyzed AminocarbonylationSami Chniti0László Kollár1Attila Bényei2Attila Takács3Department of Inorganic Chemistry, University of Pécs, Ifjúság útja 6, H-7624 Pecs, HungaryDepartment of Inorganic Chemistry, University of Pécs, Ifjúság útja 6, H-7624 Pecs, HungaryDepartment of Pharmaceutical Chemistry, University of Debrecen, Egyetem tér 1, H-4032 Debrecen, HungaryDepartment of Inorganic Chemistry, University of Pécs, Ifjúság útja 6, H-7624 Pecs, HungaryThe aminocarbonylation of 6-iodoquinoline has been investigated in the presence of large series of amine nucleophiles, providing an efficient synthetic route for producing various quinoline-6-carboxamide and quinoline-6-glyoxylamide derivatives. It was shown, after detailed optimization study, that the formation of amides and ketoamides is strongly influenced by the reaction conditions. Performing the reactions at 40 bar of carbon monoxide pressure in the presence of Pd(OAc)<sub>2</sub>/2 PPh<sub>3</sub>, the corresponding 2-ketocarboxamides were formed as major products (up to 63%). When the monodentate triphenylphosphine was replaced by the bidentate XantPhos, the quinoline-6-carboxamide derivatives were synthesized almost exclusively under atmospheric conditions (up to 98%). The isolation and characterization of the new carbonylated products of various structures were also accomplished. Furthermore, the structure of three new mono- and double-carbonylated compounds were unambiguously established by using a single-crystal XRD study.https://www.mdpi.com/1420-3049/27/1/4double carbonylationpalladiumaminocarbonylation6-iodoquinolinecarbon monoxide |
| spellingShingle | Sami Chniti László Kollár Attila Bényei Attila Takács Highly Selective Synthesis of 6-Glyoxylamidoquinoline Derivatives via Palladium-Catalyzed Aminocarbonylation Molecules double carbonylation palladium aminocarbonylation 6-iodoquinoline carbon monoxide |
| title | Highly Selective Synthesis of 6-Glyoxylamidoquinoline Derivatives via Palladium-Catalyzed Aminocarbonylation |
| title_full | Highly Selective Synthesis of 6-Glyoxylamidoquinoline Derivatives via Palladium-Catalyzed Aminocarbonylation |
| title_fullStr | Highly Selective Synthesis of 6-Glyoxylamidoquinoline Derivatives via Palladium-Catalyzed Aminocarbonylation |
| title_full_unstemmed | Highly Selective Synthesis of 6-Glyoxylamidoquinoline Derivatives via Palladium-Catalyzed Aminocarbonylation |
| title_short | Highly Selective Synthesis of 6-Glyoxylamidoquinoline Derivatives via Palladium-Catalyzed Aminocarbonylation |
| title_sort | highly selective synthesis of 6 glyoxylamidoquinoline derivatives via palladium catalyzed aminocarbonylation |
| topic | double carbonylation palladium aminocarbonylation 6-iodoquinoline carbon monoxide |
| url | https://www.mdpi.com/1420-3049/27/1/4 |
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