Premium
Annulative Synthesis of Thiazoles and Oxazoles from Alkenyl Sulfoxides and Nitriles via Additive Pummerer Reaction
Author(s) -
Hori Mitsuki,
Nogi Keisuke,
Nagaki Aiichiro,
Yorimitsu Hideki
Publication year - 2019
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.201900169
Subject(s) - chemistry , ketene , pummerer rearrangement , annulation , sulfoxide , organic chemistry , medicinal chemistry , combinatorial chemistry , acetic anhydride , catalysis
Pummerer‐based annulation of alkenyl sulfoxides, mainly ketene dithioacetal monoxides (KDMs), with nitriles has been developed. By means of trifluoromethanesulfonic anhydride (Tf 2 O) as an activator, additive Pummerer reaction and subsequent C−S‐bond‐forming cyclization from the nitrilium intermediates furnished the corresponding thiazoles. Moreover, the nitrilium intermediates proved to be interrupted intermolecularly by H 2 O to afford oxazoles instead of thiazoles.