Synthesis of ( S )‐3‐heteroaryl‐2‐hydroxy‐l‐propyl benzoates by ‘ring switching’ methodology | Zendy

Mihelič Damjana | Zendy; Jakše Renata | Zendy; Svete Jurij | Zendy; Stanovnik Branko | Zendy; Grdadolnik Simona GoliČ | Zendy

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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

( 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.

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