Facile One-pot Protocol of Derivatization Nitropyridines: Access to 3-Acetamidopyridin-2-yl 4-methylbenzenesulfonate Derivatives
This paper discloses an efficient one-pot protocol to convert easily accessible 3-nitropyridines to 3-acetamidopyridin-2-yl 4-methylbenzenesulfonate derivatives which are core structures of many pharmaceutical molecules. The strategy successfully combined a three-step reaction in one pot via progres...
| Main Authors: | , , , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
De Gruyter
2019-12-01
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| Series: | Heterocyclic Communications |
| Subjects: | |
| Online Access: | https://doi.org/10.1515/hc-2019-0017 |
| _version_ | 1818692471616438272 |
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| author | Lin Ling Chen Xiaoguang Zhao Junhao Lin Suitao Ma Guojian Liao Xiaojian Feng Pengju |
| author_facet | Lin Ling Chen Xiaoguang Zhao Junhao Lin Suitao Ma Guojian Liao Xiaojian Feng Pengju |
| author_sort | Lin Ling |
| collection | DOAJ |
| description | This paper discloses an efficient one-pot protocol to convert easily accessible 3-nitropyridines to 3-acetamidopyridin-2-yl 4-methylbenzenesulfonate derivatives which are core structures of many pharmaceutical molecules. The strategy successfully combined a three-step reaction in one pot via progressively adding different reactants at rt. The reaction displays good functional group tolerance and regioselectivity. Structurally diversified 3-nitropyridine could be time-efficiently (3.5 h) derivatized to various functional 2-O,3-N-pyridines which are apt for further elaborations. The transformation was amenable to gram-scale synthesis. |
| first_indexed | 2024-12-17T12:58:19Z |
| format | Article |
| id | doaj.art-c301626e2a9b482f9b456cabf5e3fcd9 |
| institution | Directory Open Access Journal |
| issn | 2191-0197 |
| language | English |
| last_indexed | 2024-12-17T12:58:19Z |
| publishDate | 2019-12-01 |
| publisher | De Gruyter |
| record_format | Article |
| series | Heterocyclic Communications |
| spelling | doaj.art-c301626e2a9b482f9b456cabf5e3fcd92022-12-21T21:47:26ZengDe GruyterHeterocyclic Communications2191-01972019-12-0125113814510.1515/hc-2019-0017Facile One-pot Protocol of Derivatization Nitropyridines: Access to 3-Acetamidopyridin-2-yl 4-methylbenzenesulfonate DerivativesLin Ling0Chen Xiaoguang1Zhao Junhao2Lin Suitao3Ma Guojian4Liao Xiaojian5Feng Pengju6Department of Chemistry, Jinan University, Guangzhou, 510632ChinaDepartment of Chemistry, Jinan University, Guangzhou, 510632ChinaDepartment of Chemistry, Jinan University, Guangzhou, 510632ChinaDepartment of Chemistry, Jinan University, Guangzhou, 510632ChinaDepartment of Chemistry, Jinan University, Guangzhou, 510632ChinaDepartment of Chemistry, Jinan University, Guangzhou, 510632ChinaDepartment of Chemistry, Jinan University, Guangzhou, 510632ChinaThis paper discloses an efficient one-pot protocol to convert easily accessible 3-nitropyridines to 3-acetamidopyridin-2-yl 4-methylbenzenesulfonate derivatives which are core structures of many pharmaceutical molecules. The strategy successfully combined a three-step reaction in one pot via progressively adding different reactants at rt. The reaction displays good functional group tolerance and regioselectivity. Structurally diversified 3-nitropyridine could be time-efficiently (3.5 h) derivatized to various functional 2-O,3-N-pyridines which are apt for further elaborations. The transformation was amenable to gram-scale synthesis.https://doi.org/10.1515/hc-2019-0017one-pot[3,3]-sigmatropic rearrangementheteroarenepyridine derivativeslate-stage functionalization |
| spellingShingle | Lin Ling Chen Xiaoguang Zhao Junhao Lin Suitao Ma Guojian Liao Xiaojian Feng Pengju Facile One-pot Protocol of Derivatization Nitropyridines: Access to 3-Acetamidopyridin-2-yl 4-methylbenzenesulfonate Derivatives Heterocyclic Communications one-pot [3,3]-sigmatropic rearrangement heteroarene pyridine derivatives late-stage functionalization |
| title | Facile One-pot Protocol of Derivatization Nitropyridines: Access to 3-Acetamidopyridin-2-yl 4-methylbenzenesulfonate Derivatives |
| title_full | Facile One-pot Protocol of Derivatization Nitropyridines: Access to 3-Acetamidopyridin-2-yl 4-methylbenzenesulfonate Derivatives |
| title_fullStr | Facile One-pot Protocol of Derivatization Nitropyridines: Access to 3-Acetamidopyridin-2-yl 4-methylbenzenesulfonate Derivatives |
| title_full_unstemmed | Facile One-pot Protocol of Derivatization Nitropyridines: Access to 3-Acetamidopyridin-2-yl 4-methylbenzenesulfonate Derivatives |
| title_short | Facile One-pot Protocol of Derivatization Nitropyridines: Access to 3-Acetamidopyridin-2-yl 4-methylbenzenesulfonate Derivatives |
| title_sort | facile one pot protocol of derivatization nitropyridines access to 3 acetamidopyridin 2 yl 4 methylbenzenesulfonate derivatives |
| topic | one-pot [3,3]-sigmatropic rearrangement heteroarene pyridine derivatives late-stage functionalization |
| url | https://doi.org/10.1515/hc-2019-0017 |
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