Intramolecular acylation of 3‐oxo‐2‐piperidine‐propionic acid derivatives. Synthesis of hexahydro‐2‐oxopyrano[3,2‐ b ]pyridines | Zendy

Bosch Joan | Zendy; Bonjoch Josep | Zendy; Serret Isabel | Zendy

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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.

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