β-Lactam-Synthon-Interceded, Facile, One-Pot, Diastereoselective Synthesis of Functionalized Tetra/Octahydroisoquinolone Derivatives

✍ Scribed by Raghu Raj; Vishu Mehra; Pardeep Singh; Vipan Kumar; Gaurav Bhargava; Mohinder P. Mahajan; Sachin Handa; LeGrande M. Slaughter

• Publisher: John Wiley and Sons
• Year: 2011
• Tongue: English
• Weight: 324 KB
• Volume: 2011
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.201100130

✦ Synopsis

Abstract

The convenient and facile synthesis of tetra/octahydroisoquinolones has been developed and validated by using inter/intramolecular amidolysis of racemic N‐aryl‐β‐lactams followed by intramolecular iodocyclization protocols. Thesingle‐pot synthetic version of the desired conversion was successfully developed. The single‐pot synthesis of tetrahydro‐4__H__‐isoquinoline‐1,3‐diones invariably resulted in aromatic electrophilic iodination rather than the desired iodocyclization in cases where N‐phenyl‐2‐azetidinones were employed as the synthetic precursors.