De Novo Synthesis of Polysubstituted 3-Hydroxypyridines Via “Anti-Wacker”-Type Cyclization
We report an efficient method to prepare polysubstituted 3-hydroxypyridines from amino acids, propargyl alcohols, and arylboronic acids. The process involves Pd(0)-catalyzed <i>anti</i>-selective arylative cyclizations of <i>N</i>-propargyl-<i>N</i>-tosyl-aminoald...
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| Format: | Article |
| Language: | English |
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MDPI AG
2023-02-01
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| Series: | Catalysts |
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| Online Access: | https://www.mdpi.com/2073-4344/13/2/319 |
| _version_ | 1797621825075675136 |
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| author | Kazuya Ito Takayuki Doi Hirokazu Tsukamoto |
| author_facet | Kazuya Ito Takayuki Doi Hirokazu Tsukamoto |
| author_sort | Kazuya Ito |
| collection | DOAJ |
| description | We report an efficient method to prepare polysubstituted 3-hydroxypyridines from amino acids, propargyl alcohols, and arylboronic acids. The process involves Pd(0)-catalyzed <i>anti</i>-selective arylative cyclizations of <i>N</i>-propargyl-<i>N</i>-tosyl-aminoaldehydes with arylboronic acids (“anti-Wacker”-type cyclization), oxidation of the resulting 5-substituted-3-hydroxy-1,2,3,6-tetrahydropyridines to 3-oxo derivatives, and elimination of <i>p</i>-toluenesulfinic acid. This method provides diverse polysubstituted 3-hydroxypyridines, whose hydroxy group can be further substituted by a cross-coupling reaction via a triflate. |
| first_indexed | 2024-03-11T09:02:31Z |
| format | Article |
| id | doaj.art-f5d691650a41443badf6ec1353d1bc6a |
| institution | Directory Open Access Journal |
| issn | 2073-4344 |
| language | English |
| last_indexed | 2024-03-11T09:02:31Z |
| publishDate | 2023-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Catalysts |
| spelling | doaj.art-f5d691650a41443badf6ec1353d1bc6a2023-11-16T19:41:28ZengMDPI AGCatalysts2073-43442023-02-0113231910.3390/catal13020319De Novo Synthesis of Polysubstituted 3-Hydroxypyridines Via “Anti-Wacker”-Type CyclizationKazuya Ito0Takayuki Doi1Hirokazu Tsukamoto2Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aza-Aoba, Aramaki, Aoba-ku, Sendai 980-8578, JapanGraduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aza-Aoba, Aramaki, Aoba-ku, Sendai 980-8578, JapanGraduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aza-Aoba, Aramaki, Aoba-ku, Sendai 980-8578, JapanWe report an efficient method to prepare polysubstituted 3-hydroxypyridines from amino acids, propargyl alcohols, and arylboronic acids. The process involves Pd(0)-catalyzed <i>anti</i>-selective arylative cyclizations of <i>N</i>-propargyl-<i>N</i>-tosyl-aminoaldehydes with arylboronic acids (“anti-Wacker”-type cyclization), oxidation of the resulting 5-substituted-3-hydroxy-1,2,3,6-tetrahydropyridines to 3-oxo derivatives, and elimination of <i>p</i>-toluenesulfinic acid. This method provides diverse polysubstituted 3-hydroxypyridines, whose hydroxy group can be further substituted by a cross-coupling reaction via a triflate.https://www.mdpi.com/2073-4344/13/2/319“anti-Wacker”-type cyclization3-hydroxypyridinearylboronic acidspalladiumamino acidspropargyl alcohols |
| spellingShingle | Kazuya Ito Takayuki Doi Hirokazu Tsukamoto De Novo Synthesis of Polysubstituted 3-Hydroxypyridines Via “Anti-Wacker”-Type Cyclization Catalysts “anti-Wacker”-type cyclization 3-hydroxypyridine arylboronic acids palladium amino acids propargyl alcohols |
| title | De Novo Synthesis of Polysubstituted 3-Hydroxypyridines Via “Anti-Wacker”-Type Cyclization |
| title_full | De Novo Synthesis of Polysubstituted 3-Hydroxypyridines Via “Anti-Wacker”-Type Cyclization |
| title_fullStr | De Novo Synthesis of Polysubstituted 3-Hydroxypyridines Via “Anti-Wacker”-Type Cyclization |
| title_full_unstemmed | De Novo Synthesis of Polysubstituted 3-Hydroxypyridines Via “Anti-Wacker”-Type Cyclization |
| title_short | De Novo Synthesis of Polysubstituted 3-Hydroxypyridines Via “Anti-Wacker”-Type Cyclization |
| title_sort | de novo synthesis of polysubstituted 3 hydroxypyridines via anti wacker type cyclization |
| topic | “anti-Wacker”-type cyclization 3-hydroxypyridine arylboronic acids palladium amino acids propargyl alcohols |
| url | https://www.mdpi.com/2073-4344/13/2/319 |
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