55153-12-3Relevant academic research and scientific papers
Fast-Synthesis of α-Phosphonyloxy Ketones as Drug Scaffolds in a Capillary Microreactor
Ramanjaneyulu, Bandaru T.,Vidyacharan, Shinde,Yim, Se Jun,Kim, Dong-Pyo
supporting information, p. 7730 - 7734 (2019/12/24)
A simple, room temperature approach for the fast single-step synthesis of α-phosphonyloxy ketone, a drug scaffold, has been developed which involves highly reactive species i.e., 1,2-dicarbonyls that readily react with trialkyl phosphites and formic acids in batch as well as in continuous-flow with the flow rate of 3 ml/min (tR = ～4 s). The present approach reduced the synthesis time from hours to minutes in batch, which was further lowered to a few seconds precisely controlled by single capillary microfluidics. A wide range of 1,2-dicarbonyl derivatives were smoothly transformed to their corresponding α-phosphonyloxy ketones in moderate to good yields (50–82 %) under optimized flow-reaction conditions. Further, the α-phosphonyloxy ketones produced can be utilized in batch process to form benzoin, oxazole core, and α,α′-diarylated carbonyl compounds in 82 %, 50 %, and 54 % yields, respectively, which are alternative key precursors/scaffolds of natural products and active pharmaceutical ingredients (APIs).
Facile Gold-Catalyzed Heterocyclization of Terminal Alkynes and Cyanamides Leading to Substituted 2-Amino-1,3-Oxazoles
Rassadin, Valentin A.,Boyarskiy, Vadim P.,Kukushkin
supporting information, p. 3502 - 3505 (2015/07/28)
Facile gold-catalyzed heterocyclization based upon intermolecular trapping of the generated α-oxo gold carbenes with various cyanamides R2R3NCN (R2/R3 = Alk/Alk, -(CH2)2O(CH2)2-, Ar/Ar, Ar/H) has been developed. In most cases, 2-amino-1,3-oxazoles functionalized at the nitrogen atom as well as at the fifth position of the heterocyclic ring (12 examples) were isolated in good to moderate yields.
Synthesis and catalytic applications of an extended range of tethered ruthenium(II)/η6-arene/diamine complexes
Hodgkinson, Roy,Jurk, Vclav,Zanotti-Gerosa, Antonio,Nedden, Hans Günter,Blackaby, Andrew,Clarkson, Guy J.,Wills, Martin
supporting information, p. 5517 - 5524 (2015/02/19)
A series of novel enantiopure Ru(II) complexes containing a chiral diamine and η6-arene connected by a tethering group have been prepared and were evaluated in the asymmetric reductions of a range of ketones. Changes to the level of steric hindrance and the addition of an electron-withdrawing functionality on the sulfonyl group have a significant effect on the reactivity and enantioselectivity of the catalysts.
Activity of 6-aryl-pyrrolo[2,3-d]pyrimidine-4-amines to Tetrahymena
Kaspersen, Svein Jacob,Hoff, Bard Helge,Sundby, Eirik,Charnock, Colin
, p. 35 - 41,7 (2020/07/30)
A series 6-aryl-pyrrolo[2,3-d]pyrimidine-4-amines (43 compounds), some of which are epidermal growth factor tyrosine kinase inhibitors, were tested for their protozoal toxicity using an environmental Tetrahymena strain as model organism. The protozoacidal activity of the analogues was found to be highly dependent on a 4-hydroxyl group at the 6-aryl ring, and a chiral 1-phenylethanamine substituent in position 4. Further, the potency was affected by the aromatic substitution pattern of the phenylethanamine: the unsubstituted, the meta-fluoro and the para-bromo substituted derivatives had the lowest minimum protozoacidal concentrations (8-16 μg/mL). Surprisingly, both enantiomers were found to have high potency suggesting that this compound class could have several modes of action. No correlation was found between the compounds protozoacidal activity and the in vitro epidermal growth factor receptor tyrosine kinase inhibitory potency. This suggests that the observed antimicrobial effects are related to other targets. Testing towards a panel of kinases indicated several alternative modes of action.
A sustainable byproduct catalyzed domino strategy: Facile synthesis of α-formyloxy and acetoxy ketones via iodination/nucleophilic substitution/hydrolyzation/oxidation sequences
Zhu, Yan-Ping,Gao, Qing-He,Lian, Mi,Yuan, Jing-Jing,Liu, Mei-Cai,Zhao, Qin,Yang, Yan,Wu, An-Xin
supporting information; experimental part, p. 12700 - 12702 (2012/01/03)
The sustainable byproduct catalyzed domino strategy has been performed for the facile synthesis of α-formyloxy and acetoxy ketones via iodination/nucleophilic substitution/hydrolyzation/oxidation sequences from simple and readily available aromatic ketone
Synthesis and biological evaluation of 5-substituted and 4,5-disubstituted-2-arylamino oxazole TRPV1 antagonists
Perner, Richard J.,Koenig, John R.,Didomenico, Stanley,Gomtsyan, Arthur,Schmidt, Robert G.,Lee, Chih-Hung,Hsu, Margaret C.,McDonald, Heath A.,Gauvin, Donna M.,Joshi, Shailen,Turner, Teresa M.,Reilly, Regina M.,Kym, Philip R.,Kort, Michael E.
scheme or table, p. 4821 - 4829 (2010/08/06)
The synthesis and structure-activity relationships of a series of 5-monosubstituted and 4,5-disubstituted 2-arylaminooxazoles as novel antagonists of the transient receptor potential vanilloid 1 (TRPV1) receptor are described. The 7-hydroxy group of the t
The reaction of terminal alkynes with PhI(OAc)2: a convenient procedure for the preparation of α-acyloxy ketones
Mo, Dong-Liang,Dai, Li-Xin,Hou, Xue-Long
supporting information; experimental part, p. 5578 - 5581 (2011/02/22)
Treatment of terminal alkynes with PhI(OAc)2 in different acids at 70 °C provided the corresponding α-acyloxy ketones in good to excellent yields. A plausible mechanism has been proposed based on the experimental results.
One-pot synthesis of α-formyloxy ketones from enolizable ketones
Kumar, Sunil,Kumar, Ashok,Gupta, Rakesh K.,Kumar, Devinder
, p. 338 - 345 (2008/04/01)
One-pot synthesis of α-formyloxy tones as well as α-acetoxy ketones from enolizable ketones and [hydroxy(tosyloxy) iodo] benzene (HTIB)/polymer supported [hydroxy(tosyloxy) iodo] benzene (PSHTIB) in N,N-dimethylformamide (DMF)/N, N-dimethylacetamide (DMA)
Asymmetric transfer hydrogenation of ketones catalyzed by hydrophobic metal-amido complexes in aqueous micelles and vesicles
Wang, Fei,Liu, Hui,Cun, Linfeng,Zhu, Jin,Deng, Jingen,Jiang, Yaozhong
, p. 9424 - 9429 (2007/10/03)
Asymmetric transfer hydrogenation of ketones, especially α-bromomethyl aromatic ketones, catalyzed by unmodified, hydrophobic transition metal-amido complexes (TsDPEN-M), was performed successfully with significant enhancement of activity, chemoselectivity, and enantio-selectivity (up to 99% ee) in aqueous media containing micelles and vesicles. The hydrophobic catalyst, embedded in micelles constructed from the surfactant cetyltrimethylammonium bromide (CTAB), could be separated from the organic phase along with the products and was recycled for at least six times.
Asymmetric transfer hydrogenation of prochiral ketones in aqueous media with new water-soluble chiral vicinal diamine as ligand
Ma, Yaping,Liu, Hui,Chen, Li,Cui, Xin,Zhu, Jin,Deng, Jingen
, p. 2103 - 2106 (2007/10/03)
(Matrix presented) An easily accessible water-soluble chiral o-sulfonated 1,2-diphenylethlenediamine 2 and its mono-N-tosylated derivative 3 were synthesized for the first time. The ruthenium-complex-catalyzed reduction of prochiral ketones in aqueous media has been examined by using 3 as ligand and sodium formate as the source of hydrogen. The asymmetric transfer hydrogenation of ω-bromo acetophenones was achieved, in which only formate displacement occurred when formic acid/triethylamine azeotrope was used as the hydrogen donor.
