Transformation reactions of the Betti base analog aminonaphthols

By means of simple or domino ring-closure reactions of 1-(alpha-aminobenzyl)-2-naphthol (Betti base: 1), 1-aminomethyl-2-naplithol (2) and 2-(alpha-aminobenzyl)-1-naphthol (reverse Berri base: 3) with phosgene, ethyl benzimidate, 2-carboxybenzaldehyde, levulinic acid, salicylaldehyde/formalin or salicylaldehyde/acetaldehyde, naphth[1,2-e][1,3]oxazine and naphth[2,1-e][1,3]oxazine derivatives were prepared. All of the nitrogen-bridged polycyclic derivatives of 1 and 3 containing a number of centers of asymmetry were formed with nearly complete diastereoselectivity. Considerable differences were observed in the ring-closing abilities of the unsubstituted and phenyl-substituted aminonaphthols 1 and 2 and of the regioisomeric compounds 1 and 3.