35960-75-9Relevant articles and documents
Photoinduced Decarboxylative Radical Addition Reactions for Late Stage Functionalization of Peptide Substrates
Fernandez-Rodriguez, Patricia,Legros, Fabien,Maier, Thomas,Weber, Angelika,Méndez, María,Derdau, Volker,Hessler, Gerhard,Kurz, Michael,Villar-Garea, Ana,Ruf, Sven
supporting information, p. 782 - 787 (2021/01/21)
Photoredox chemistry has greatly stimulated the application of radical based transformations in medicinal chemistry and early drug discovery in recent years. Carboxylate groups have been identified as traceless leaving groups that can be converted into radical intermediates capable of undergoing 1,4-conjugate addition reactions to Michael acceptors. Herein, we show the successful C-terminal derivatization of small peptide substrates by using this methodology in a parallel synthesis setting. Finally, we outline a general strategy for the γ-homologation of several drugs derived from α-amino acids in a late stage functionalization (LSF) approach.
An unprecedented cobalt-catalyzed selective aroylation of primary amines with aroyl peroxides
Li, Dong,Li, Jiale,Li, Juanjuan,Yuan, Songdong,Zhang, Qian
, (2020/09/16)
A novel and facile cobalt-catalyzed selective aroylation of primary amines with aroyl peroxides was developed for the synthesis of aryl amides. It was unprecedented that C[sbnd]N bond formation product was selectively generated without the common N[sbnd]O bond formation product. Aroyl peroxides act as the sole aroylation reagent without additional base or oxidant. The reactions proceeded under mild conditions and showed broad substrates scope with a series of primary amines and aroyl peroxides.
Synthesis of Medium-Ring-Sized Benzolactams by Using Strong Electrophiles and Quantitative Evaluation of Ring-Size Dependency of the Cyclization Reaction Rate
Kurouchi, Hiroaki,Ohwada, Tomohiko
, p. 876 - 901 (2019/12/30)
Benzolactams with medium-sized rings were synthesized via the electrophilic aromatic substitution reaction of carbamoyl cations (R1R2N+═C═O) in good to high yields without dilution. These reactions were utilized to quantitatively examine the extent of retardation of medium-sized ring formation, compared to five- or six-membered ring formation. The order of reaction rates of formation of cyclic benzolactams is six- > five- > seven- > eight- > nine-membered ring at 25 °C. The present reaction provides a route to eight- A nd nine-membered benzolactams.
