A practical two-step procedure for the preparation of enantiopure pyridines: Multicomponent reactions of alkoxyallenes, nitriles and carboxylic acids followed by a cyclocondensation reaction
A practical approach to highly functionalized 4-hydroxypyridine derivatives with stereogenic side chains in the 2- and 6-positions is described. The presented two-step process utilizes a multicomponent reaction of alkoxyallenes, nitriles and carboxylic acids to provide β-methoxy-β-ketoenamides which...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2011-07-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.7.108 |
| _version_ | 1818954394321813504 |
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| author | Christian Eidamshaus Roopender Kumar Mrinal K. Bera Hans-Ulrich Reissig |
| author_facet | Christian Eidamshaus Roopender Kumar Mrinal K. Bera Hans-Ulrich Reissig |
| author_sort | Christian Eidamshaus |
| collection | DOAJ |
| description | A practical approach to highly functionalized 4-hydroxypyridine derivatives with stereogenic side chains in the 2- and 6-positions is described. The presented two-step process utilizes a multicomponent reaction of alkoxyallenes, nitriles and carboxylic acids to provide β-methoxy-β-ketoenamides which are transformed into 4-hydroxypyridines in a subsequent cyclocondensation. The process shows broad substrate scope and leads to differentially substituted enantiopure pyridines in good to moderate yields. The preparation of diverse substituted lactic acid derived pyrid-4-yl nonaflates is described. Additional evidence for the postulated mechanism of the multicomponent reaction is presented. |
| first_indexed | 2024-12-20T10:21:28Z |
| format | Article |
| id | doaj.art-d09835f644024142ae6f776e54bae43c |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-20T10:21:28Z |
| publishDate | 2011-07-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-d09835f644024142ae6f776e54bae43c2022-12-21T19:43:55ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972011-07-017196297510.3762/bjoc.7.1081860-5397-7-108A practical two-step procedure for the preparation of enantiopure pyridines: Multicomponent reactions of alkoxyallenes, nitriles and carboxylic acids followed by a cyclocondensation reactionChristian Eidamshaus0Roopender Kumar1Mrinal K. Bera2Hans-Ulrich Reissig3Freie Universität Berlin, Institut für Chemie und Biochemie, Takustr. 3, D-14195 Berlin, GermanyFreie Universität Berlin, Institut für Chemie und Biochemie, Takustr. 3, D-14195 Berlin, GermanyFreie Universität Berlin, Institut für Chemie und Biochemie, Takustr. 3, D-14195 Berlin, GermanyFreie Universität Berlin, Institut für Chemie und Biochemie, Takustr. 3, D-14195 Berlin, GermanyA practical approach to highly functionalized 4-hydroxypyridine derivatives with stereogenic side chains in the 2- and 6-positions is described. The presented two-step process utilizes a multicomponent reaction of alkoxyallenes, nitriles and carboxylic acids to provide β-methoxy-β-ketoenamides which are transformed into 4-hydroxypyridines in a subsequent cyclocondensation. The process shows broad substrate scope and leads to differentially substituted enantiopure pyridines in good to moderate yields. The preparation of diverse substituted lactic acid derived pyrid-4-yl nonaflates is described. Additional evidence for the postulated mechanism of the multicomponent reaction is presented.https://doi.org/10.3762/bjoc.7.108allenesenantiopure pyridinesketoenamidesmulticomponent reactionsnonaflates |
| spellingShingle | Christian Eidamshaus Roopender Kumar Mrinal K. Bera Hans-Ulrich Reissig A practical two-step procedure for the preparation of enantiopure pyridines: Multicomponent reactions of alkoxyallenes, nitriles and carboxylic acids followed by a cyclocondensation reaction Beilstein Journal of Organic Chemistry allenes enantiopure pyridines ketoenamides multicomponent reactions nonaflates |
| title | A practical two-step procedure for the preparation of enantiopure pyridines: Multicomponent reactions of alkoxyallenes, nitriles and carboxylic acids followed by a cyclocondensation reaction |
| title_full | A practical two-step procedure for the preparation of enantiopure pyridines: Multicomponent reactions of alkoxyallenes, nitriles and carboxylic acids followed by a cyclocondensation reaction |
| title_fullStr | A practical two-step procedure for the preparation of enantiopure pyridines: Multicomponent reactions of alkoxyallenes, nitriles and carboxylic acids followed by a cyclocondensation reaction |
| title_full_unstemmed | A practical two-step procedure for the preparation of enantiopure pyridines: Multicomponent reactions of alkoxyallenes, nitriles and carboxylic acids followed by a cyclocondensation reaction |
| title_short | A practical two-step procedure for the preparation of enantiopure pyridines: Multicomponent reactions of alkoxyallenes, nitriles and carboxylic acids followed by a cyclocondensation reaction |
| title_sort | practical two step procedure for the preparation of enantiopure pyridines multicomponent reactions of alkoxyallenes nitriles and carboxylic acids followed by a cyclocondensation reaction |
| topic | allenes enantiopure pyridines ketoenamides multicomponent reactions nonaflates |
| url | https://doi.org/10.3762/bjoc.7.108 |
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