Synthesis of (S)-3-heteroaryl-2-hydroxy-l-propyl benzoates by 'ring switching' methodology

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Synthesis of (S)-3-heteroaryl-2-hydroxy-l-propyl benzoates by 'ring switching' methodology

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

Journal of heterocyclic chemistry, 11/2001, Volume: 38, Issue: 6

Journal Article

(S)‐5‐Benzoyloxymethyl‐3‐(E)‐(dimethylamino)methylidenetetrahydrofuran‐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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Mihelič, Damjana | Jakše, Renata | Svete, Jurij | Stanovnik, Branko | Grdadolnik, Simona GoliČ

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