5997-56-8Relevant academic research and scientific papers
Regio- and chemoselective rearrangement of terminal epoxides into methyl alkyl and aryl ketones
Tian, Yingying,Jürgens, Eva,Kunz, Doris
, p. 11340 - 11343 (2018/10/31)
The development of the highly active pincer-type rhodium catalyst 2 for the nucleophilic Meinwald rearrangement of functionalised terminal epoxides into methyl ketones under mild conditions is presented. An excellent regio- and chemoselectivity is obtained for the first time for aryl oxiranes.
Substrate-Controlled Product Divergence: Conversion of CO2 into Heterocyclic Products
Rintjema, Jeroen,Epping, Roel,Fiorani, Giulia,Martín, Eddy,Escudero-Adán, Eduardo C.,Kleij, Arjan W.
, p. 3972 - 3976 (2016/03/19)
Substituted epoxy alcohols and amines allow substrate-controlled conversion of CO2 into a wide range of heterocyclic structures through different mechanistic manifolds. This new approach results in an unusual scope of CO2-derived products by initial activation of CO2 through either the amine or alcohol unit, thus providing nucleophiles for intramolecular epoxy ring opening under mild reaction conditions. Control experiments support the crucial role of the amine/alcohol fragment in this process with the nucleophile-assisted ring-opening step following an SNi pathway, and a 5-exo-tet cyclization, thus leading to heterocyclic scaffolds.
NIS-mediated ring-closure/opening cascade reactions of allylamides: An expedient route to oxazolines
Hu, Yancheng,Li, Xincheng,Wan, Boshun
, p. 6935 - 6943 (2015/08/24)
An unprecedented NIS-mediated ring-closure/opening cascade reaction of allylamides is developed. The substrates with various functionalities were well tolerated and the scope can be extended to allylic carboxylates. Notably, the resulting iodinated chain
M-CPBA-Mediated Intramolecular Aminohydroxylation of N-Sulfonyl Aminoalkenes to Synthesize β-Hydroxyl Cyclic Amines
Yin, Yan,Zhou, Hong,Sun, Guofeng,Liu, Xichen
, p. 1337 - 1345 (2015/10/06)
A variety of structurally diverse N-sulfonyl-protected aminoalkenes readily reacted with m-CPBA to produce a series of β-hydroxyl cyclic amines in high yields through intramolecular aminohydroxylation. This metal-free and easy-to-handle synthetic methodol
Copper-catalyzed trifluoromethylation and cyclization of aromatic-sulfonyl-group-tethered alkenes for the construction of 1,2-benzothiazinane dioxide type compounds
Dong, Xiang,Sang, Rui,Wang, Qiang,Tang, Xiang-Ying,Shi, Min
, p. 16910 - 16915 (2014/01/06)
A multi-talented system: An efficient copper-catalyzed tandem trifluoromethylation/annulation of an electron-deficient aromatic ring has been developed. This method provides a powerful and straightforward way to synthesize trifluoromethylated 1,2-benzothiazinane dioxides under mild conditions (see scheme). The mechanism was investigated by a series of kinetic experiments and isotopic labeling studies.
Phosphorylated hydroxyethylamines as novel inhibitors of the bacterial cell wall biosynthesis enzymes MurC to MurF
Sova, Matej,Kovac, Andreja,Turk, Samo,Hrast, Martina,Blanot, Didier,Gobec, Stanislav
experimental part, p. 217 - 222 (2010/03/01)
Enzymes involved in the biosynthesis of bacterial peptidoglycan represent important targets for development of new antibacterial drugs. Among them, Mur ligases (MurC to MurF) catalyze the formation of the final cytoplasmic precursor UDP-N-acetylmuramyl-pentapeptide from UDP-N-acetylmuramic acid. We present the design, synthesis and biological evaluation of a series of phosphorylated hydroxyethylamines as new type of small-molecule inhibitors of Mur ligases. We show that the phosphate group attached to the hydroxyl moiety of the hydroxyethylamine core is essential for good inhibitory activity. The IC50 values of these inhibitors were in the micromolar range, which makes them a promising starting point for the development of multiple inhibitors of Mur ligases as potential antibacterial agents. In addition, 1-(4-methoxyphenylsulfonamido)-3-morpholinopropan-2-yl dihydrogen phosphate 7a was discovered as one of the best inhibitors of MurE described so far.
Titanium(III)-induced intramolecular radical cyclization of epoxyallene ethers: an efficient method for synthesis of multifunctional tetrahydrofurans
Xu, Lubin,Huang, Xian
, p. 500 - 503 (2008/04/13)
Ti(III)-mediated intramolecular free radical cyclization of epoxyallene ethers in an exo-mode was studied. The reaction afforded an efficient and highly regioselective method of synthetically important 3-vinyl-4-hydroxymethyl tetrahydrofurans.
Syhthesis of the tetrahydropteridine-2,4-dione having a substituted methyl group at 6-position
Tada, Masaru,Shimamura, Tomoyuki,Suzuki, Takeaki
, p. 2511 - 2517 (2007/10/03)
Lewis acid treatment of 5-amino-6-(N-2,3-epoxypropyl-N-tosyl)amino-1,3-dimethyluracil (3) gave the diazepine (4) fused to uracil ring, and the tosylate (5) from 4 underwent ring transformation to provide tetrahydropteridinediones (7 and 8) depending on th
The First Practical Method of Selective Heteroatom-Directed Chlorohydroxylation
Lai, Jin-Yu,Wang, Fu-Song,Guo, Guang-Zhong,Dai, Li-Xin
, p. 6944 - 6946 (2007/10/02)
A new Pd(II)-catalyzed nucleophilic chlorohydroxylation reaction of allylic amines and sulfides was achieved, and the regioselective reaction gives high yields of the chlorohydrin products, which can be transformed into epoxy compounds or aziridine compou
