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A convergent, umpoled synthesis of 2-(1-amidoalkyl)pyridines
A convenient, one-pot, two-component synthesis of 2-(1-amidoalkyl)pyridines is reported, based upon the substitution of suitably-activated pyridine N-oxides by azlactone nucleophiles, followed by decarboxylative azlactone ring-opening. The synthesis obviates the need for precious metal catalysts to...
| Autores principales: | , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
Beilstein-Institut
2016
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| Materias: | |
| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4734400/ https://www.ncbi.nlm.nih.gov/pubmed/26877802 http://dx.doi.org/10.3762/bjoc.12.1 |
| _version_ | 1782412914218500096 |
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| author | Johnson, Tarn C Marsden, Stephen P |
| author_facet | Johnson, Tarn C Marsden, Stephen P |
| author_sort | Johnson, Tarn C |
| collection | PubMed |
| description | A convenient, one-pot, two-component synthesis of 2-(1-amidoalkyl)pyridines is reported, based upon the substitution of suitably-activated pyridine N-oxides by azlactone nucleophiles, followed by decarboxylative azlactone ring-opening. The synthesis obviates the need for precious metal catalysts to achieve a formal enolate arylation reaction, and constitutes a formally ‘umpoled’ approach to this valuable class of bioactive structures. |
| format | Online Article Text |
| id | pubmed-4734400 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2016 |
| publisher | Beilstein-Institut |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-47344002016-02-12 A convergent, umpoled synthesis of 2-(1-amidoalkyl)pyridines Johnson, Tarn C Marsden, Stephen P Beilstein J Org Chem Letter A convenient, one-pot, two-component synthesis of 2-(1-amidoalkyl)pyridines is reported, based upon the substitution of suitably-activated pyridine N-oxides by azlactone nucleophiles, followed by decarboxylative azlactone ring-opening. The synthesis obviates the need for precious metal catalysts to achieve a formal enolate arylation reaction, and constitutes a formally ‘umpoled’ approach to this valuable class of bioactive structures. Beilstein-Institut 2016-01-04 /pmc/articles/PMC4734400/ /pubmed/26877802 http://dx.doi.org/10.3762/bjoc.12.1 Text en Copyright © 2016, Johnson and Marsden https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms) |
| spellingShingle | Letter Johnson, Tarn C Marsden, Stephen P A convergent, umpoled synthesis of 2-(1-amidoalkyl)pyridines |
| title | A convergent, umpoled synthesis of 2-(1-amidoalkyl)pyridines |
| title_full | A convergent, umpoled synthesis of 2-(1-amidoalkyl)pyridines |
| title_fullStr | A convergent, umpoled synthesis of 2-(1-amidoalkyl)pyridines |
| title_full_unstemmed | A convergent, umpoled synthesis of 2-(1-amidoalkyl)pyridines |
| title_short | A convergent, umpoled synthesis of 2-(1-amidoalkyl)pyridines |
| title_sort | convergent, umpoled synthesis of 2-(1-amidoalkyl)pyridines |
| topic | Letter |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4734400/ https://www.ncbi.nlm.nih.gov/pubmed/26877802 http://dx.doi.org/10.3762/bjoc.12.1 |
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