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Thiaindanones III. beckmann rearrangement of oximes
Author(s) -
Aparajithan K.,
Thompson A. C.,
Sam Joseph
Publication year - 1966
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.5570030415
Subject(s) - beckmann rearrangement , chemistry , yield (engineering) , oxime , alkyl , stereochemistry , medicinal chemistry , organic chemistry , materials science , metallurgy
The Beckmann rearrangement of 5‐methylthiaindan‐4‐one oximes (I) and thiaindan‐6‐one oximes (IV) proceeds with the migration of the alkyl group to yield dihydrothieno‐pyridones (II and V, respectively). In two instances, the corresponding lactones (VIIa and VIIb) also were isolated. None of the isomeric lactams (X and XI) were isolated from the Beckmann rearrangement reactions. Supporting evidence for the proposed structures is provided.