65753-90-4Relevant academic research and scientific papers
Photoinduced Remote Functionalization of Amides and Amines Using Electrophilic Nitrogen Radicals
Morcillo, Sara P.,Dauncey, Elizabeth M.,Kim, Ji Hye,Douglas, James J.,Sheikh, Nadeem S.,Leonori, Daniele
supporting information, p. 12945 - 12949 (2018/09/14)
The selective functionalization of C(sp3)?H bonds at distal positions to functional groups is a challenging task in synthetic chemistry. Reported here is a photoinduced radical cascade strategy for the divergent functionalization of amides and protected amines. The process is based on the oxidative generation of electrophilic amidyl radicals and their subsequent transposition by 1,5-H-atom transfer, resulting in remote fluorination, chlorination and, for the first time, thioetherification, cyanation, and alkynylation. The process is tolerant of most common functional groups and delivers useful building blocks that can be further elaborated. The utility of this strategy is demonstrated through the late-stage functionalization of amino acids and a dipeptide.
Ruthenium-catalyzed reduction of N-alkoxy- and N-hydroxyamides
Fukuzawa, Hiroko,Ura, Yasuyuki,Kataoka, Yasutaka
experimental part, p. 3643 - 3648 (2011/12/02)
A ruthenium-catalyzed reduction of N-alkoxy- and N-hydroxyamides was found to afford corresponding amides in good to high yields. A simple RuCl 3/Zn-Cu/alcohol system, without the addition of any other ligands, exhibited a high catalytic activity, and therefore the present reaction does not require a stoichiometric amount of metals or metal complexes as reductants. When β-substituted-α,β-unsaturated N-methoxyamides were employed as substrates, concurrent hydrogenation of the olefin moiety proceeded slowly with deprotection of the methoxy group. In the reduction of N-hydroxyamides, the alcoholic solvent was found to function as a hydrogen donor.
Lawesson's reagent for direct thionation of hydroxamic acids: Substituent effects on LR reactivity
Przychodzen, Witold
, p. 676 - 684 (2007/10/03)
To explore the generality and scope of direct thionation of hydroxamic acids (HAs), the reaction of various structurally diverse HAs with Lawesson's reagent was investigated. The yield of thiohydroxamic acid (THAs) is poor when HAs possess bulky acyl and/or N-substituents, acidic α-hydrogen atoms, or an N-phenyl ring. THAs yields were correlated with Brown sigma parameter. The relative rates of two subsequent processes kT2 and kR2 were also measured. Correlation was also found for methine proton chemical shifts of N-isopropyl benzothiohydroxamic acids.
