4492-50-6Relevant academic research and scientific papers
Effects of backbone rigidification on intramolecular hydrogen bonding in a family of diamides
Liang, Gui-Bai,Desper, John M.,Gellman, Samuel H.
, p. 925 - 938 (1993)
In an effort to gain insight on the balance of noncovalent forces that controls the adoption of folded conformations in small molecules, we have examined intramolecular hydrogen bond formation in a series of diamides containing a variety of conformational
Direct Copper-Catalyzed Three-Component Synthesis of Sulfonamides
Chen, Yiding,Murray, Philip R. D.,Davies, Alyn T.,Willis, Michael C.
supporting information, p. 8781 - 8787 (2018/07/29)
First introduced into medicines in the 1930s, the sulfonamide functional group continues to be present in a wide range of contemporary pharmaceuticals and agrochemicals. Despite their popularity in the design of modern bioactive molecules, the underpinning methods for sulfonamide synthesis are essentially unchanged since their introduction, and rely on the use of starting materials with preinstalled sulfur-functionality. Herein we report a direct single-step synthesis of sulfonamides that combines two of the largest monomer sets available in discovery chemistry, (hetero)aryl boronic acids and amines, along with sulfur dioxide, using a Cu(II) catalyst, to deliver a broad range of sulfonamides. Sulfur dioxide is provided by the surrogate reagent DABSO. The reaction tolerates broad variation in both coupling partners, including aryl, heteroaryl and alkenyl boronic acids, as well as cyclic and acyclic alkyl secondary amines, and primary anilines. We validate the method by showing that a variety of drugs, and drug-fragments, can be incorporated into the process.
Selective α-Oxyamination and Hydroxylation of Aliphatic Amides
Li, Xinwei,Lin, Fengguirong,Huang, Kaimeng,Wei, Jialiang,Li, Xinyao,Wang, Xiaoyang,Geng, Xiaoyu,Jiao, Ning
, p. 12307 - 12311 (2017/09/11)
Compared to the α-functionalization of aldehydes, ketones, even esters, the direct α-modification of amides is still a challenge because of the low acidity of α-CH groups. The α-functionalization of N?H (primary and secondary) amides, containing both an unactived α-C?H bond and a competitively active N?H bond, remains elusive. Shown herein is the general and efficient oxidative α-oxyamination and hydroxylation of aliphatic amides including secondary N?H amides. This transition-metal-free chemistry with high chemoselectivity provides an efficient approach to α-hydroxy amides. This oxidative protocol significantly enables the selective functionalization of inert α-C?H bonds with the complete preservation of active N?H bond.
Dodecacarbonyltriruthenium catalyzed one-to-one addition of N-substituted formamides to olefins
Tsuji, Yasushi,Yoshii, Seiji,Ohsumi, Tatsuya,Kondo, Teruyuki,Watanabe, Yoshihisa
, p. 379 - 386 (2007/10/02)
Dodecacarbonyltriruthenium (Ru3(CO)12) showed high catalyitic activity for the first one-to-one addition of N-substituted formamides to both terminal and internal olefins at 180-200 deg C under a carbon monoxide pressure of 20 kg cm-2.The addit
