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Synthesis of ( S )‐3‐heteroaryl‐2‐hydroxy‐l‐propyl benzoates by ‘ring switching’ methodology
Author(s) -
Mihelič Damjana,
Jakše Renata,
Svete Jurij,
Stanovnik Branko,
Grdadolnik Simona GoliČ
Publication year - 2001
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.5570380610
Subject(s) - chemistry , benzoates , dimethylamine , tetrahydrofuran , ring (chemistry) , medicinal chemistry , curtius rearrangement , stereochemistry , organic chemistry , solvent
Abstract ( S )‐5‐Benzoyloxymethyl‐3‐[( E )‐(dimethylamino)methylidene]tetrahydrofuran‐2‐one (6), prepared in 5 steps from L‐glutamic acid (1), was used as precursor in a one step ‘ring switching’ synthesis of ( S )‐2‐hydroxy‐3‐heteroaryl‐l‐propyl benzoates 13‐18, 23, 24. In the reaction of 6 with 2‐aminopyridine (21) and 2‐amino‐4,6‐dimethylpyrimidine (22) the corresponding dimethylamine substitution products (25, 26) were obtained.