2,6-Epoxy-3-benzazocines: Centrally active N/O-acetals by cyclization of amino- and amidoacetals

Article abstract of DOI:10.1002/ardp.19933260303

Under acidic conditions the secondary amines 10a and 10b, the primary amine 15, the amide 17a, and the urethane 17b were cyclized to yield the 2,6-epoxy-3-benzazocines 11a, 11b, 16, 18a and 18b, respectively. Ring closure of the inverse amide 5a, however, failed to give the tricyclic N/O-acetal 6. With LiAlH₄ the epoxy bridge of the urethane 18b was opened to afford the bicyclic 3-benzazocine 20. - While the N-(2-methoxyethyl) derivative 11b did not influence the behaviour of mice, the N-methyl derivative 11a showed strong central effects.