[2,6-Epoxy-3-benzazocines: centrally acting N/O-acetals produced by cyclization of amino- and amidoacetals].
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.
Wünsch
B
B
Institut für Pharmazie und Lebensmittelchemie der Universität München.
Höfner
G
G
Bauschke
G
G
D000818:Animals; D001575:Benzomorphans / Q000138:chemical synthesis* / Q000494:pharmacology; D002491:Central Nervous System Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D003500:Cyclization; D051379:Mice
D001575:Benzomorphans; D002491:Central Nervous System Agents
2,6-Epoxy-3-benzazocine: Zentral wirksame N/O-Acetale durch Ringschluss von Amino- und Amidoacetalen.