35010-10-7Relevant academic research and scientific papers
Synthesis of α-diketones from alkylaryl- and diarylalkynes using mercuric salts
Jung, Michael E.,Deng, Gang
supporting information, p. 2142 - 2145 (2014/05/06)
Both alkylarylalkynes and diarylalkynes 1 are converted into the α-diketones 2 in good yield by the use of mercuric salts, e.g., mercuric nitrate hydrate or mercuric triflate, in the presence of water. Other mercuric salts, e.g., sulfate, chloride, acetate, or trifluoroacetate, do not provide the diketone product. A possible mechanism is proposed.
Synthesis and antiplasmodial activity of new indolone N-Oxide derivatives
Nepveu, Fran?oise,Kim, Sothea,Boyer, Jeremie,Chatriant, Olivier,Ibrahim, Hany,Reybier, Karine,Monje, Marie-Carmen,Chevalley, Severine,Perio, Pierre,Lajoie, Barbora H.,Bouajila, Jalloul,Deharo, Eric,Sauvain, Michel,Tahar, Rachida,Basco, Leonardo,Pantaleo, Antonella,Turini, Francesco,Arese, Paolo,Valentin, Alexis,Thompson, Eloise,Vivas, Livia,Petit, Serge,Nallet, Jean-Pierre
experimental part, p. 699 - 714 (2010/07/09)
A series of 66 new indolone-N-oxide derivatives was synthesized with three different methods. Compounds were evaluated for in vitro activity against CQ-sensitive (3D7), CQ-resistant (FcB1), and CQ and pyrimethamine cross-resistant (K1) strains of Plasmodium falciparum (P.f.), aswell as for cytotoxic concentration (CC50) on MCF7 and KB human tumor cell lines. Compound 26 (5-methoxy-indolone-N-oxide analogue) had the most potent antiplasmodial activity in vitro (50 MCF7/IC50 FcB1: 14623; CC50 KB/IC50 3D7: 198823). In in vivo experiments, compound 1 (dioxymethylene derivatives of the indolone-N-oxide) showed the best antiplasmodial activity against Plasmodium berghei, 62% inhibition of the parasitaemia at 30 mg/kg/day. 2009 American Chemical Society.
Mild oxidation of diarylacetylenes to 1,2-diketones using oxone in trifluoroacetic acid
Chu, Jean-Ho,Chen, Yen-Ju,Wu, Ming-Jung
experimental part, p. 2155 - 2162 (2009/12/27)
A variety of 1,2-diaryldiketones were synthesized in 15-90% yields by treatment of diarylacetylenes with Oxone as the oxidant in trifluoroacetic acid. Oxidation of 1-nitro-2-(phenylethynyl) benzene and 2,4￠-(ethyne-1,2-diyl) bis(nitrobenzene) furnished 1-benzoylbenzo[c]isoxazol-3(1H)-one and benzo[c]isoxazol-3-yl(4-nitrophenyl)methanone as the major products, respectively. Georg Thieme Verlag Stuttgart.
Access to unsymmetrical 1,2-diketone intermediates via benzeneseleninic anhydride-promoted oxidation: Application to indolone-N-oxide synthesis
Boyer, Jeremie,Bernardes-Genisson, Vania,Nepveu, Francoise
, p. 507 - 508 (2007/10/03)
1,2-Dicarbonyl compounds employed as key-intermediates in indolone-N-oxide synthesis were prepared by direct oxidation of aryl, aryl- and aryl, alkyl-substituted alkenes assisted by benzeneseleninic anhydride.
A new general approach for the synthesis of 2-substituted-3H-indol-3-one N-oxide derivatives
Ge?nisson, Vania Bernardes,Bouniol, Anne-Vale?rie,Nepveu, Franc?oise
, p. 700 - 702 (2007/10/03)
2-aryl (phenyl, 1,3-benzodioxolyl) and 2-alkyl (ethyl, sec-butyl)-3H-indol-3-one N-oxides were synthesized by a new general method involving a reductive intramolecular cyclization reaction of ortho-diketo nitrobenzene derivatives.
CONVENIENT PREPARATION OF UNSYMMETRICALLY SUBSTITUTED BENZILS BY PERMANGANATE OXIDATION OF β-OXO PHOSPHORUS YLIDES
Aitken, R. Alan,Cadogan, J. I. G.,Gosney, Ian
, p. 281 - 286 (2007/10/02)
Oxidative cleavage of a range of ylides 4 with R1 and/or R2 being aromatic groups, using KMnO4 in a two-phase system, affords unsymmetrical benzils and 1-arylpropane-1,2-diones 5 in moderate to good yield, and the ylide formation and oxidation can be combined in a convenient one-pot method.Key words: Phosphorus ylides, oxidation, 1,2-diketones, benzils, permanganate, oxoalkylidenetriphenylphosphoranes.
A Facile One-Pot Synthesis of Vicinal Di- and Triketones from α-Methylene Ketones by NBS-DMSO Oxidation
Tatsugi, Jiro,Izawa, Yasuji
, p. 2747 - 2763 (2007/10/02)
The reaction of 1,2-diarylethanones (1a-u) with N-bromosuccinimide in anhydrous dimethyl sulphoxide afforded diarylethanediones (2a-u) in excellent yields.Under similar conditions, 1-phenyl-2-butanone (3) gave 1-phenyl-1,2-butanedione (4) in fair yield in addition to a small amount of 1-phenyl-3-methylthio-1,2-butanedione (5) and 1-phenyl-1-methylthio-2-butanone (6). 4-Phenyl-2-butanone (7), 1,3-diphenyl-2-propanone (9), and 1,3-diphenyl-1,3-propanedione (10) gave the corresponding triketones monohydrate (8) and (11). 1-Indanone (12), 2-indanone (13), and 1,3-indandione (14) gave ninhydrin (15) in good yields.In the case of 3-phenyl-1-indanone (16), 3-phenyl-2-bromo-1-indanone (17), 3-phenyl-2-bromo-1-indenone (18) and 3-phenyl-1-indenone (19) were obtained. 1-Phenyl-1-propanone (20) and 1-phenyl-1-butanone (22) gave the corresponding α-(methylthio)ketones (21) and (22). 1,3,3-Triphenylpropanone (24a) and 1-phenyl-3-methyl-1-butanone (24b) yielded only the corresponding α-bromoketones (25a,b) in good yields.These α-bromoketones, however, afforded the corresponding α-diketones (26a,b) in moderate yields when α-bromoketones reacted with dimethyl sulphoxide in the presence of AgBF4.
