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Synthesis and biological evaluation of novel spirocyclic â-lactams from reaction of pyrrolidine-2-carboxylic acid and benzyl amine

L.N. Sharada,G.S.Satyanarayana Reddy, B.Sammaiah, D.Sumalatha

A practical synthesis of spirocyclic 2-azetidinones or â–lactams (rotamers) starting fromnatural proline is described. á- Hydroxymethyl-N-Boc proline (4) has been converted via benzyl amide (5) and spiro-fused 2-azetidinones (6) into 2-(benzyl)-2,5-diaza-spiro[3.4] octan-1-one (7) onBoc deprotection. Which on further N-alkylations with various 2-chloromethyl pyridines to yield N-alkylated title compounds (8a-e). 1H NMR and 13C NMR clearly indicated that spiro- â -lactams are in rotamers.