1-Alkyl- and (卤)-1,2-Dialkyl-2,3-dihydro-1,8-naphthyridin-4(1H)-ones by a Tandem Michael鈥揝NAr Annulation Reaction

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• 作者：Richard A. Bunce ; Scott T. Squires ; Baskar Nammalwar
• 刊名：The Journal of Organic Chemistry
• 出版年：2013
• 出版时间：March 1, 2013
• 年：2013
• 卷：78
• 期：5
• 页码：2144-2148
• 全文大小：249K
• 年卷期：v.78,no.5(March 1, 2013)
• ISSN：1520-6904

文摘

A tandem Michael鈥揝_NAr annulation reaction has been developed for the synthesis of 1-alkyl and (卤)-1,2-dialkyl-2,3-dihydro-1,8-naphthyridin-4(1H)-ones. Treatment of 1-(2-chloropyridin-3-yl)prop-2-en-1-one (R = H) or (E or Z)-1-(2-chloropyridin-3-yl)but-2-en-1-one (R = CH₃) with R鈥睳H₂ in DMF at 50 掳C for 24 h provides 2,3-dihydro-1,8-naphthyridin-4(1H)-ones in 65鈥?5% yields. Mechanistic studies suggest that the reaction sequence is initiated by Michael addition to the side chain enone.