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

著者 Muthukrishnan I , Vinoth P , Vivekanand T , Nagarajan S , Maheswari CU , Menéndez JC , Sridharan V
J Org Chem.2015 Dec 22 ; ():.
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A highly efficient synthesis of 5,6-dihydrodibenzo[b,h][1,6]naphthyridines was achieved by the reaction between 2-(N-propargylamino)benzaldehydes and arylamines in the presence of CuBr2. The in situ generated electron-deficient heterodienes bearing a tethered alkyne partner underwent intramolecular inverse electron-demand hetero Diels-Alder reaction (IEDDA) 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.
PMID: 26694659 [PubMed - as supplied by publisher]
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