Preparation of N-Alkylated Pyridones via Selective N-Alkylation of 2-Alkoxypyridines on Solid Phase

Regioselective solid-phase synthesis of N-alkylated 2-pyridones has been carried out starting from 2-halopyridines. Variously substituted 2-halopyridines were linked to a Wang resin in quantitative yields to afford 2-alkoxypyridines. The coupled products were then reacted with a variety of alkyl hal...

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Published inJournal of combinatorial chemistry Vol. 4; no. 5; pp. 530 - 535
Main Authors Ruda, Marcus C, Bergman, Jan, Wu, Jinchang
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.09.2002
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Applied
Chemistry, Medicinal
Chemistry, Multidisciplinary
Life Sciences & Biomedicine
Medicin och hälsovetenskap
Pharmacology & Pharmacy
Physical Sciences
Science & Technology
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Summary:Regioselective solid-phase synthesis of N-alkylated 2-pyridones has been carried out starting from 2-halopyridines. Variously substituted 2-halopyridines were linked to a Wang resin in quantitative yields to afford 2-alkoxypyridines. The coupled products were then reacted with a variety of alkyl halides, resulting in tandem alkylation and cleavage from the resin to generate N-alkylated pyridones with no detectable traces of O-alkylated products. The scope and limitations of this exceptionally selective reaction have been studied.
Bibliography:ObjectType-Article-1
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ISSN:1520-4766
1520-4774
1520-4774
DOI:10.1021/cc020036i