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Ru II ‐Catalyzed ortho ‐Sulfonamidation of α‐Tetralones with Sulfonyl Azides and Synthesis of Sivelestat by Aromatic C−H Activation
Author(s) -
Krishna Rao Medikonda V.,
Reddy Keesari Nagarjuna,
Sridhar Balasubramaniam,
Subba Reddy Basi V.
Publication year - 2017
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201700356
Subject(s) - chemistry , tetralones , sulfonyl , catalysis , regioselectivity , medicinal chemistry , stereochemistry , organic chemistry , alkyl
A method has been developed for the sulfonamidation of tetralones and 1,4‐naphthoquinones by using sulfonyl azides in the presence of a Ru II /Ag I catalytic system. In case of tetralones, C−H bond functionalization occurred exclusively at the ortho position, whereas 1,4‐addition was the main transformation for 1,4‐naphthoquinones. This method is highly regioselective and was successfully utilized for the synthesis of sivelestat, an inhibitor of human neutrophil elastase.