329939-82-4Relevant academic research and scientific papers
Poly(methylhydrosiloxane) as a green reducing agent in organophosphorus-catalysed amide bond formation
Hamstra, Daan F. J.,Lenstra, Danny C.,Koenders, Tjeu J.,Rutjes, Floris P. J. T.,Mecinovi?, Jasmin
supporting information, p. 6426 - 6432 (2017/08/10)
Development of catalytic amide bond formation reactions has been the subject of the intensive investigations in the past decade. Herein we report an efficient organophosphorus-catalysed amidation reaction between unactivated carboxylic acids and amines. Poly(methylhydrosiloxane), a waste product of the silicon industry, is used as an inexpensive and green reducing agent for in situ reduction of phosphine oxide to phosphine. The reported method enables the synthesis of a wide range of secondary and tertiary amides in very good to excellent yields.
Direct oxidative amidation of aldehydes with amines catalyzed by heteropolyanion-based ionic liquids under solvent-free conditions via a dual-catalysis process
Fu, Renzhong,Yang, Yang,Zhang, Jin,Shao, Jintao,Xia, Xuming,Ma, Yunsheng,Yuan, Rongxin
, p. 1784 - 1793 (2016/02/10)
A simple and efficient procedure for the synthesis of amides directly from aldehydes and amines catalyzed by heteropolyanion-based ionic liquids under solvent-free conditions has been reported. The practical protocol was found to tolerate a wide range of substrates with different functional groups. Moderate to excellent yields, solvent-free media, and operational simplicity are the main highlights. The proposed dual-catalysis mechanistic pathway was briefly investigated. Furthermore, the heteropolyanion-based ionic liquids were easily reusable for this oxidative amidation.
An efficient, eco-friendly and sustainable tandem oxidative amidation of alcohols with amines catalyzed by heteropolyanion-based ionic liquids via a bifunctional catalysis process
Fu, Renzhong,Yang, Yang,Feng, Wei,Ge, Qiuxia,Feng, Yan,Zeng, Xiaojun,Chai, Wen,Yi, Jun,Yuan, Rongxin
, p. 8319 - 8326 (2016/12/02)
An efficient, eco-friendly and sustainable method for the tandem oxidative amidation of alcohols with amines has been reported. Using heteropolyanion-based ionic liquids as the catalyst and tert-butyl hydroperoxide as the oxidant, this amidation reaction is operationally straightforward and provides a series of primary, secondary and tertiary amides derivatives in moderate to good yields. Solvent-free media, microwave-promoted conditions and reusability of catalysts are the main highlights. Further, the proposed bifunctional catalysis mechanistic pathway has been briefly investigated in this report.
Degradable conjugates from oxanorbornadiene reagents
Kislukhin, Alexander A.,Higginson, Cody J.,Hong, Vu P.,Finn
supporting information; experimental part, p. 6491 - 6497 (2012/05/07)
Oxanorbornadienedicarboxylate (OND) reagents were explored for purposes of binding and releasing drugs from serum albumins as representative macromolecular carriers. Being highly reactive Michael acceptors, ONDs form adducts with thiols and amines, which then undergo retro-Diels-Alder fragmentation. A study of more than 30 model adducts revealed a number of modifications that can be used to influence adduct stability. For the most reactive OND linkers, the labeling of the single available bovine serum albumin (BSA) cysteine residue was complete within minutes at a mid-micromolar concentration of reactants. While a selectivity of greater than 1000-fold for thiol over amine was observed with model amino acids, the labeling of protein amines with ONDs is fast enough to be practical, as demonstrated by the reaction with thiol-depleted BSA. The OND-amine adducts were found to be up to 15 times more stable than OND-thiol adducts, and to be sensitive to acid by virtue of a stereochemically dependent acceleration of cycloreversion. The release rate of fluorescent cargo from serum albumins was tuned by selecting the coupling partners: the available half-lives ranged from 40 min to 7 days at 37 °C. Such versatility of release profiles from protein carriers, controlled by the nature of the OND linkage, is a useful addition to the drug delivery toolbox.
Synthesis of N -Acyl-5-aminopenta-2,4-dienals via base-induced ring-opening of N -acylated furfurylamines: Scope and limitations
Ouairy, Cecile,Michel, Patrick,Delpech, Bernard,Crich, David,Marazano, Christian
supporting information; experimental part, p. 4311 - 4314 (2010/09/04)
N-Acylation of furfurylamines provided 1, which on double deprotonation with LDA led to the formation of N-acyl-5-aminopenta-2,4-dienals 2 via an isomerization involving opening of the furan ring. The scope and limitations of the procedure were examined by considering the influence of substituents on the carbonyl group and also on the heterocycle moiety. The efficacy of the reaction was shown to be very dependent on the nature of these groups.
