64785-81-5Relevant academic research and scientific papers
Unlocking Amides through Selective C–N Bond Cleavage: Allyl Bromide-Mediated Divergent Synthesis of Nitrogen-Containing Functional Groups
Govindan, Karthick,Chen, Nian-Qi,Chuang, Yu-Wei,Lin, Wei-Yu
, p. 9419 - 9424 (2021/11/30)
We report a new set of reactions based on the unlocking of amides through simple treatment with allyl bromide, creating a common platform for accessing a diverse range of nitrogen-containing functional groups such as primary amides, sulfonamides, primary amines, N-acyl compounds (esters, thioesters, amides), and N-sulfonyl esters. The method has potential industrial applicability, as demonstrated through gram-scale syntheses in batch and in a continuous flow system.
Copper-Catalyzed Electrophilic Amidation of Organotrifluoroborates with Use of N-Methoxyamides
Banjo, Shona,Nakasuji, Eiko,Meguro, Tatsuhiko,Sato, Takaaki,Chida, Noritaka
, p. 7941 - 7947 (2019/05/24)
A copper-catalyzed electrophilic amidation of aryltrifluoroborates with use of N-methoxyamides is reported. The reaction shows high functional group compatibility derived from two distinct features: 1) the high stability of the N-methoxyamides and 2) the nonbasic mild conditions in the presence of LiCl. The developed method can also be applied to the synthesis of enamides, which are widely distributed in natural products. Preliminary mechanistic studies suggest that the initial step is the transmetalation of the aryltrifluoroborate by the assistance of LiCl, and the resulting aryl copper intermediate provides the anilide through non-SN2 oxidative addition to the N-methoxyamide and subsequent reductive elimination.
Antibacterial activity of a novel series of 3-bromo-4-(1H-3-indolyl)-2,5-dihydro-1H-2,5-pyrroledione derivatives - An extended structure-activity relationship study
Mahboobi, Siavosh,Eichhorn, Emerich,Winkler, Matthias,Sellmer, Andreas,Moellmann, Ute
, p. 633 - 656 (2008/09/19)
Compounds containing 3-bromo-2,5-dihydro-1H-2,5-pyrroledione and indole substructures were found to have antibacterial activity against resistant strains of Staphylococcus aureus and some other Gram positive bacteria. The investigated compounds exhibit mi
Efficient synthesis of trisimidazole and glutaric acid bearing porphyrins: Ligands for active-site models of bacterial nitric oxide reductase
Collman, James P.,Yan, Yi-Long,Lei, Jianping,Dinolfo, Peter H.
, p. 923 - 926 (2007/10/03)
Ligands (1) for active-site models of bacterial nitric oxide reductase (NOR) have been efficiently synthesized. These compounds (1) feature three imidazolyl moieties and one carboxylic acid residue at the FeB site, which represent the closest available synthetic model ligands of NOR active center. The stereo conformations of these ligands are established on the basis of steric effects and 1H NMR chemical shifts under the ring current effect of the porphyrin.
Mercaptoamide-based non-hydroxamic acid type histone deacetylase inhibitors
Anandan, Sampath-Kumar,Ward, John S.,Brokx, Richard D.,Bray, Mark R.,Patel, Dinesh V.,Xiao, Xiao-Xi
, p. 1969 - 1972 (2007/10/03)
Inhibitors of histone deacetylases (HDAC) are emerging as a promising class of anti-cancer agents. A mercaptoamide functionality was designed as a bidentate zinc chelator and incorporated into the hydroxamic acid based SAHA (1) scaffold in order to identify non-hydroxamate compounds as potential inhibitors of histone deacetylases. Two sets of mercaptoamides 2 and 3 with varying spacer length were synthesized and their HDAC inhibitory activity was evaluated. Low micromolar inhibition was observed for mercaptoamides 2e, 3b, and 3d.
