6028-38-2Relevant articles and documents
Convenient synthesis of various substituted homotaurines from alk-2-enamides
Nai, Youfeng,Xu, Jiaxi
, p. 1355 - 1365 (2013/08/23)
Various substituted homotaurines (=3-aminopropane-1-sulfonic acids) 6 were readily synthesized in satisfactory to good yields via the Michael addition of thioacetic acid to alk-2-enamides 3 (→4), followed by LiAlH4 reduction (→5) and performic acid oxidation (Scheme 1). The configuration of 'anti'-disubstituted homotaurine 'anti'-6h was deduced from the 3-(acetylthio)alkanamide (=S-(3-amino-1,2-dimethyl-3-oxopropyl) ethanethioate)'anti'-4h formed in the Michael addition, which was identified via the Karplus equation analysis, and confirmed by X-ray diffraction analysis. The current route is an efficient method to synthesize diverse substituted homotaurines, including 1-, 2-, and N-monosubstituted, as well as 1,2-, 1,N-, 2,N-, and N,N-disubstituted homotaurines (Table). Copyright
Aromatic borylation/amidation/oxidation: A rapid route to 5-substituted 3-amidophenols
Shi, Feng,Smith III, Milton R.,Maleczka Jr., Robert E.
, p. 1411 - 1414 (2007/10/03)
5-Substituted 3-amidophenols are prepared by subjecting 3-substituted halobenzenes to an Ir-catalyzed aromatic borylation, followed by a Pd-catalyzed amidation, and finally an oxidation of the boronic ester intermediate. The entire C-H activation borylation/amidation/oxidation sequence can be accomplished without isolation of any intermediate arenes. Usefully, amide partners can include lactams, carbamates, and ureas.
