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Formation of a Tetracyclic Isoquinoline Derivative by Rearrangement of a [(Bromophenyl)butyryl]oxazolidinone
Author(s) -
Roydhouse Mark D.,
Walton John C.
Publication year - 2007
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.200600918
Subject(s) - chemistry , isoquinoline , derivative (finance) , domino , stereochemistry , sequence (biology) , cope rearrangement , pericyclic reaction , labelling , medicinal chemistry , organic chemistry , catalysis , biochemistry , financial economics , economics
Treatment of 3‐[4‐(2‐bromophenyl)‐2‐phenylbutyryl]‐4,4‐dimethyloxazolidin‐2‐one with LDA in THF launched a domino rearrangement sequence ending in the assembly of a tetracyclic cyclopentaoxazolo[3,2‐ b ]isoquinolin‐6‐one derivative. Two mechanisms involving an S RN 1‐type process were proposed. EPR spectroscopic and 13 C‐labelling experiments suggested that both were operative.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)