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Synthesis of (2 S )‐2‐(Benzoylamino)‐3‐(heteroaryl)propyl Benzoates
Author(s) -
Škof Marko,
Svete Jurij,
Stanovnik Branko,
GoličGrdadolnik Simona
Publication year - 2000
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/(sici)1522-2675(20000412)83:4<760::aid-hlca760>3.0.co;2-r
Subject(s) - benzoates , chemistry , hydroxymethyl , medicinal chemistry , stereochemistry , organic chemistry
(3 E ,5 S )‐1‐Benzoyl‐5‐[(benzoyloxy)methyl]‐3‐[(dimethylamino)methylidene]pyrrolidin‐2‐one ( 9 ) was prepared in two steps from commercially available ( S )‐5‐(hydroxymethyl)pyrrolidin‐2‐one ( 7 ) ( Scheme 1 ). Compound 9 gave, in one step, upon treatment with various C,N‐ and C,O‐1,3‐dinucleophiles 10 – 18 , the corresponding 3‐(quinolizin‐3‐yl)‐ and 3‐(2‐oxo‐2 H ‐pyran‐3‐yl)‐substituted (2 S )‐2‐(benzoylamino)propyl benzoates 19 – 27 ( Schemes 1 and 2 ).