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Intramolecular acylation of 3‐oxo‐2‐piperidine‐propionic acid derivatives. Synthesis of hexahydro‐2‐oxopyrano[3,2‐ b ]pyridines
Author(s) -
Bosch Joan,
Bonjoch Josep,
Serret Isabel
Publication year - 1982
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.5570190308
Subject(s) - chemistry , acylation , intramolecular force , bicyclic molecule , enol , piperidine , intramolecular reaction , stereochemistry , organic chemistry , medicinal chemistry , catalysis
The intramolecular acylation of some δ‐keto acids derived from 3‐oxo‐2‐piperidinepropionic acid are described. Bicyclic enol lactones coming from an O ‐acylation reaction are obtained in all cases. The regioselec‐tivity of these processes is discussed in terms of the acylating agent and the δ‐keto acid structure. The procedure establishes a convenient synthesis of hexahydro‐2‐oxopyrano[3,2‐ b )pyridines.