6299-56-5Relevant academic research and scientific papers
Optimization of physicochemical properties is a strategy to improve drug-likeness associated with activity: Novel active and selective compounds against Trypanosoma cruzi
Amaral, Maiara,Romanelli, Maiara M.,Tempone, Andre G.,Varela, Marina T.,de Castro Levatti, Erica V.,Fernandes, Jo?o Paulo S.
, (2022/01/31)
Trypanosoma cruzi is the causing agent of Chagas disease, a parasitic infection without efficient treatment for chronic patients. Despite the efforts, no new drugs have been approved for this disease in the last 60 years. Molecular modifications based on
Electron-Catalyzed Aminocarbonylation: Synthesis of α,β-Unsaturated Amides from Alkenyl Iodides, CO, and Amines
Picard, Baptiste,Fukuyama, Takahide,Bando, Takanobu,Hyodo, Mamoru,Ryu, Ilhyong
supporting information, p. 9505 - 9509 (2021/12/09)
Aminocarbonylation of alkenyl iodides with CO and amines proceeded under heating to produce α,β-unsaturated amides in good yields (23 examples, 71% average yield). This catalyst-free method exhibited good functional-group tolerance, and open a straightforward access to functionalized acrylamides, as illustrated by the synthesis of Ilepcimide. A hybrid radical/ionic mechanism involving chain electron transfer is proposed for this transformation.
Synthesis of Linear α,β-Unsaturated Amides from Isocyanates and Alkenylaluminum Reagents
Chen, Bo,Wu, Xiao-Feng
supporting information, p. 788 - 792 (2020/05/19)
A new approach has been developed for the synthesis of linear α,β-unsaturated amides by the direct coupling of isocyanates with alkenylaluminum reagents. At room temperature, the desired α,β-unsaturated amides were isolated in good to excellent yields with good functional-group tolerance in the absence of any catalyst or additive.
Enhancing Ligand-Free Fe-Catalyzed Aminocarbonylation of Alkynes by ZrF4
Huang, Zijun,Dong, Yanan,Li, Yudong,Makha, Mohamed,Li, Yuehui
, p. 5236 - 5240 (2019/09/03)
Zirconium fluoride was utilized to promote efficiently iron-catalyzed aminocarbonylation between alkynes and amines without the use of extra ligands. In particular, this new system is applicable to a wide range of amine and alkyne substrates affording α,β-unsaturated amides in good to excellent yields. Preliminary mechanistic studies reveal the activation model involving interactions of ZF4 with both iron catalyst and amine substrates.
General and Efficient Intermolecular [2+2] Photodimerization of Chalcones and Cinnamic Acid Derivatives in Solution through Visible-Light Catalysis
Lei, Tao,Zhou, Chao,Huang, Mao-Yong,Zhao, Lei-Min,Yang, Bing,Ye, Chen,Xiao, Hongyan,Meng, Qing-Yuan,Ramamurthy, Vaidhyanathan,Tung, Chen-Ho,Wu, Li-Zhu
, p. 15407 - 15410 (2017/11/13)
[2+2] Photocycloaddition, for example, the dimerization of chalcones and cinnamic acid derivatives, is a unique strategy to construct cyclobutanes, which are building blocks for a variety of biologically active molecules and natural products. However, most attempts at the above [2+2] addition have focused on solid-state, molten-state, or host–guest systems under ultraviolet-light irradiation in order to overcome the competition of facile geometric isomerization of nonrigid olefins. We report a general and simple method to realize the intermolecular [2+2] dimerization reaction of these acyclic olefins to construct cyclobutanes in a highly regio- and diastereoselective manner in solution under visible light, which provides an efficient solution to a long-standing problem.
Practical Synthesis of Amides via Copper/ABNO-Catalyzed Aerobic Oxidative Coupling of Alcohols and Amines
Zultanski, Susan L.,Zhao, Jingyi,Stahl, Shannon S.
supporting information, p. 6416 - 6419 (2016/06/09)
A modular Cu/ABNO catalyst system has been identified that enables efficient aerobic oxidative coupling of alcohols and amines to amides. All four permutations of benzylic/aliphatic alcohols and primary/secondary amines are viable in this reaction, enabling broad access to secondary and tertiary amides. The reactions exhibit excellent functional group compatibility and are complete within 30 min-3 h at rt. All components of the catalyst system are commercially available.
Direct amidation of carboxylic acids with amines under microwave irradiation using silica gel as a solid support
Ojeda-Porras, Andrea,Hernández-Santana, Alejandra,Gamba-Sánchez, Diego
supporting information, p. 3157 - 3163 (2015/05/27)
A highly improved and green methodology for the direct amidation of carboxylic acids with amines using silica gel as a solid support and catalyst is described. The scope of this method is exemplified by the use of several aliphatic, aromatic, unsaturated and fatty acids. The reaction is also applied to different primary and secondary amines. Typically, the amines should be aliphatic, but aromatic amines can be used as well, though with lower yields. Several experiments to illustrate the selectivity of this methodology were also carried out with several more functionalized acids and amines. This approach is a substantial improvement over other previously described methods in amide synthesis.
Methylaluminoxane (MAO)-assisted direct amidation of esters
Desrat, Sandy,Ducousso, Aline,Gapil, Shelly,Remeur, Camille,Roussi, Fanny
, p. 385 - 387 (2015/02/19)
Aliphatic and aromatic esters are efficiently transformed into amides in good to excellent yields, under mild conditions using methylaluminoxane (MAO). This reaction can be performed either at room temperature or by applying microwave irradiation.
N-heterocyclic carbene-catalyzed oxidation of aldehydes for the synthesis of amides via phenolic esters
Ji, Miran,Lim, Seungyeon,Jang, Hye-Young
, p. 28225 - 28228 (2014/07/22)
N-heterocyclic carbene-catalyzed oxidation using TEMPO is reported for the conversion of aldehydes to amides. A wide range of amides were synthesized in good yields (up to 72%) via a one-pot, sequential protocol involving oxidative esterification of aldehydes and subsequent aminolysis. To promote efficient aminolysis, various alkoxide leaving groups were evaluated.
NHC-catalyzed C-O or C-N bond formation: Efficient approaches to α,β-unsaturated esters and amides
Zhang, Bo,Feng, Peng,Cui, Yuxin,Jiao, Ning
supporting information; experimental part, p. 7280 - 7282 (2012/07/28)
Simple and efficient NHC-catalyzed transformations of bromoenal or α,β-dibromoenal into α,β-unsaturated esters or amides with high stereoselectivity through C-O or C-N bond formation have been demonstrated. The NHC-catalyzed processes occur under mild con
