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Updated: Mar 6, 2026
Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
Catalytic Direct-type 1,4-Addition Reactions of Alkylazaarenes
Hirotsugu Suzuki1, Ryo Igarashi1, Yasuhiro Yamashita1
1Department of Chemistry, School of Science, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo, Japan.
Abstract:
1,4-addition reactions of alkylazaarenes catalyzed by strong Brønsted bases have been developed for the first time. The desired reactions with α,β-unsaturated amides proceeded under mild reaction conditions to give the 1,4-adducts in high yields. Both ortho- and para-substituted azaarenes afforded the desired adducts in high yields. Regioselective reactions of di- or trimethylpyridine were found to be possible depending on the acidity of the α-hydrogen atoms. Furthermore, a candidate of allosteric protein kinase modulators was synthesized in two steps. An asymmetric variant of this reaction was also found to be feasible.
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