Synthesis of 5,6-Dihydrodibenzo[b,h][1,6]naphthyridines via Copper Bromide Catalyzed Intramolecular [4 + 2] Hetero-Diels–Alder Reactions

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• 作者：Isravel Muthukrishnan ; Perumal Vinoth ; Thavaraj Vivekanand ; Subbiah Nagarajan ; C. Uma Maheswari ; J. Carlos Menéndez ; Vellaisamy Sridharan
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：February 5, 2016
• 年：2016
• 卷：81
• 期：3
• 页码：1116-1124
• 全文大小：487K
• ISSN：1520-6904

文摘

A highly efficient synthesis of 5,6-dihydrodibenzo[b,h][1,6]naphthyridines was achieved by reaction between 2-(N-propargylamino)benzaldehydes and arylamines in the presence of CuBr<sub>2sub>. The in situ generated electron-deficient heterodienes bearing a tethered alkyne partner underwent an intramolecular inverse electron-demand hetero-Diels–Alder reaction followed by air oxidation to furnish the products in high yields. This reaction tolerated a large number of substituents to afford diverse products under mild conditions. This strategy was also successfully extended to the synthesis of 12,13-dihydro-6H-benzo[h]chromeno[3,4-b][1,6]naphthyridin-6-ones starting from 3-amino-2H-chromen-2-one, again in high yields.