Premium
Tandem rearrangement involving a β‐hydroxysulfoxide and cyclization processes toward the 1‐benzenesulfonyl‐5‐benzenethio‐1,2,2a,3,4,5‐hexahydrobenz[ c,d ]indole oxygenated at the 4‐position
Author(s) -
Stamos Ioannis K.
Publication year - 1997
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570340518
Subject(s) - chemistry , trifluoroacetic anhydride , chlorobenzene , tandem , indole test , conformational isomerism , derivative (finance) , trifluoroacetic acid , stereochemistry , medicinal chemistry , organic chemistry , catalysis , molecule , materials science , financial economics , economics , composite material
Treatment of compound 4 with trifluoroacetic anhydride under reflux in chlorobenzene underwent a tandem rearrangement to produce compound 5 . When the acetylated derivative of 4 , was treated with trifluoroacetic anhydride in the presence of Lewis acids produced two cis cyclized conformers 7a and 7b , presumably through the intermediate B .