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Synthesis and rearrangements of 2,3,4,5‐tetrahydro‐3‐benzazocin‐6(1 H )ones
Author(s) -
Comer William T.,
Call John D.,
Matier W. Lesley,
Combs Charles M.,
Dykstra Stanley J.
Publication year - 1973
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570100417
Subject(s) - chemistry , intramolecular force , acylation , intermolecular force , cleavage (geology) , bond cleavage , alkylation , stereochemistry , medicinal chemistry , catalysis , organic chemistry , molecule , geotechnical engineering , fracture (geology) , engineering
The preparation of 3‐benzenesulfonyl‐ and 3‐benzoyl‐2,3,4,5‐tetrahydro‐3‐benzazoein‐6(1 H )‐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.