Darstellung und Eigenschaften von 1,2,3,4,5,6‐Hexahydro‐8‐hydroxy‐3‐methyl‐3‐benzazocin

The preparation of 3‐benzenesulfonyl‐ and 3‐benzoyl‐2,3,4,5‐tetrahydro‐3‐benzazoein‐6(1H)‐ones by intramolecular acylation is described. Acid catalyzed rearrangements of these 3‐benzazocin‐6‐ones occurs by 3,4‐bond cleavage, which is followed by intramolecular or intermolecular alkylation, to produce indanones (i.e. XIV) or a 3,4‐dihydroisoquinoline (II), respectively. In addition to spectral support for these structures, an independent synthesis of II is described from a known 3,4‐dihydroisoquinoline. Two rearrangements of 3‐benzazocin‐6‐ones under alkaline conditions are also described, and the products are again evidence for 3,4‐bond cleavage to vinylphenones. These beuzazocine rearrangements have been observed only with the 6‐keto compounds.

show abstract

Darstellung und Eigenschaften von 1,2,3,4,5,6‐Hexahydro‐8‐hydroxy‐3‐methyl‐3‐benzazocin

Abstract: In continuation of our search for new analgesics, 1,2,3,4,5,6-hexahydro-8-hydroxy-3-methyl-3-benzazocine1) has been prepared.

Cited by 7 publications

References 3 publications

Azepine Ring Systems Containing two Rings

Azepine Ring Systems Containing two Rings

ChemInform Abstract: DARST. UND EIGENSCHAFTEN VON 1,2,3,4,5,6‐HEXAHYDRO‐8‐HYDROXY‐3‐METHYL‐3‐BENZAZOCIN

Synthesis and rearrangements of 2,3,4,5‐tetrahydro‐3‐benzazocin‐6(1H)ones

Contact Info

Product

Resources

About