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β‐Lactam‐Synthon‐Interceded, Facile, One‐Pot, Diastereoselective Synthesis of Functionalized Tetra/Octahydroisoquinolone Derivatives
Author(s) -
Raj Raghu,
Mehra Vishu,
Singh Pardeep,
Kumar Vipan,
Bhargava Gaurav,
Mahajan Mohinder P.,
Handa Sachin,
Slaughter LeGrande M.
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100130
Subject(s) - synthon , chemistry , intramolecular force , tetra , halogenation , isoquinoline , combinatorial chemistry , lactam , electrophile , organic chemistry , medicinal chemistry , catalysis
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.