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Preparation of analogues of efaroxan and KU14R as potential imidazoline receptor subtype 3 ligands
Author(s) -
Farn Richard D.,
Ramsden Christopher A.,
Morgan Noel G.
Publication year - 2008
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.5570450338
Subject(s) - chemistry , imidazoline receptor , ketone , diastereomer , alcohol , halogenation , medicinal chemistry , stereochemistry , organic chemistry , medicine
The preparation and characterization of new analogues of the imidazoline insulin secretagogue efaroxan 1 are described. These include 1,2,4‐triazole, 1,3,4‐oxadiazole, pyrimidine, 1,4,5,6‐tetrahydropyrimidine and 1,2‐dihydro‐1,2,4,5‐tetrazine analogues. Bromination of 2,3‐dihydro‐2‐ethylbenzo[ b ]furan‐2‐carbonitrile 19 gives the 3,3‐dibromo analogue 28 , which is readily hydrolysed to the corresponding ketone 29 . Reduction of this ketone gives the alcohol 31 as a mixture of diastereoisomers that is converted to the fluoride 32 using diethylaminosulfur trifluoride.