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

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 CuBr2. 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...