We report herein an unprecedented Cu(II)-catalyzed divergent synthesis of naphthofurans and benzochromanes from 2-naphthols, N, N-dimethylethanolamine, and methylene-3,4-dihydroquinazolin-2(1H)-ones (or methylene-3,4-dihydroquinazolin-2(1H)-thiones) under mild conditions. With methylene-3,4-dihydroquinazolin-2(1H)-ones, naphthofuran products were afforded through an unconventional [3+1+1] cyclization while benzochromanes were obtained via a routine [3+2+1] annulation when methylene-3,4-dihydroquinazolin-2(1H)-thiones were applied as substrates. Both products could be obtained via a one-pot /two-step process starting from 2-aminoacetophenone with isocyanates or isothiocyanates.

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