Diversity-Oriented Synthesis of 1-Substituted 4-Aryl-6-oxo-1,6-dihydropyridine-3-carboxamides.
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- 作者：Jernej Ba拧kov膷 ; Georg Dahmann ; Amalija Golobi膷 ; Uro拧 Gro拧elj ; Drago Ko膷ar ; Branko Stanovnik ; Jurij Svete
- 刊名：ACS Combinatorial Science
- 出版年：2012
- 出版时间：September 10, 2012
- 年：2012
- 卷：14
- 期：9
- 页码：513-519
- 全文大小：443K
- 年卷期：v.14,no.9(September 10, 2012)
- ISSN：2156-8944
文摘
A simple five-step diversity-oriented synthesis of 1-substituted 4-aryl-6-oxo-1,6-dihydropyridine-3-carboxamides was developed. Treatment of dimethyl 2-((dimethylamino)methylidene)-3-oxopentanedioate with twenty primary amines gave 1-substituted methyl 4-hydroxy-6-oxo-1,6-dihydropyridine-3-carboxylates. Transformation into the corresponding 4-tosyloxy and 4-chloro derivatives, followed by Suzuki鈥揗iyaura arylations gave a series of eleven N-substituted methyl 4-aryl-6-oxo-1,6-dihydropyridine-3-carboxylates. Combinatorial screening was employed to establish suitable reaction conditions for Suzuki鈥揗iyaura arylation of N-alkylpyridones. Hydrolysis of the esters followed by parallel solution-phase amidation of the corresponding carboxylic acids with primary and secondary amines furnished a library of seventeen final products.