50885-07-9Relevant academic research and scientific papers
Total syntheses of cytotoxic, naturally occurring kalasinamide, geovanine, and marcanine A
Lang, Steffen,Groth, Ulrich
, p. 911 - 913 (2009)
(Chemical Equation Presented) Two novel synthetic strategies were developed for the natural products geovanine, marcanine A, and kalasinamide. The nine-step synthesis of geovanine marks its first total synthesis. The three compounds are known for their an
Photoelectrocyclization Reactions of Amidonaphthoquinones
Landward, Michael B.,Rainier, Jon D.,Yin, Jinya
, p. 4298 - 4311 (2020/04/10)
Readily available acrylamide naphthoquinones can be converted into the corresponding aza-anthraquinones using 6?-photoelectrocyclization reactions. Not only do these reactions not proceed thermally but, as demonstrated here, they can also be used to generate a range of aza-anthraquinone and aza-tetracycline derivatives including the natural products griffithazanone A and marcanine A. Several of the aza-anthraquinones generated in this work showed antibacterial activity.
Direct nitration method of electron-enriched aromatic hydrocarbons
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Paragraph 0078-0080, (2018/10/02)
The invention discloses a direct nitration method of electron-enriched aromatic hydrocarbons, and belongs to the field of organic synthesis. The direct nitration method is a novel green free radical nitration method; aromatic hydrocarbons are taken as raw materials, acetonitrile, dichloromethane, chloroform, or acetone is taken as a reaction solvent, at room temperature conditions, the raw materials and green nitration reagent tert-butyl nitrite (TBN) are subjected to free radical nitration so as to obtain nitro-aromatic compounds. According to the direct nitration method, no metal is adoptedin reaction, tert-butyl nitrite is directly adopted in nitration reaction. Electron-donating groups such as OMe are introduced, the electron density of aromatic compounds is increased, the nitration reaction possibility is increased. The using amount of tert-butyl nitrite is reduced; only a product and tert-butyl alcohol are generated, environment pollution is reduced. The direct nitration methodis promising in application prospect in the field of nitro-aromatic compound synthesis, green nitration is realized, and a novel idea is provided for large-scale industrialized nitro-aromatic compoundproduction.
Synthesis of kalasinamide, a putative plant defense phototoxin
Gandy, Michael N.,Piggott, Matthew J.
experimental part, p. 866 - 868 (2009/04/04)
The first total synthesis of the azaanthracene kalasinamide (1) is described, and the discrepancy in the reported 13C NMR data and melting points for the natural product from two different sources is resolved. Kalasinamide is prone to autosensitized photooxidation, in solution and in the solid state, to give the corresponding quinone, marcanine A (8). This transformation may be representative of a novel and more general step in the biosynthesis of (aza)anthraquinones. Through its ability to generate toxic singlet oxygen, kalasinamide may serve a protective role, defending the plant against predation and the invasion of microbial pathogens, following mechanical insult.
Photochemical nitration by tetranitromethane. Part XLI. Addition ipso to a methoxy group and the effect of methanol in the photochemical reaction between 1,4-dimethoxynaphthalene and tetranitromethane
Butts, Craig P.,Eberson, Lennart,Hartshorn, Michael P.,Persson, Ola,Thompson, Rewi S.,Robinson, Ward T.
, p. 1066 - 1077 (2007/10/03)
The photolysis of the charge transfer complex between 1,4-dimethoxynaphthalene and tetranitromethane in dichloromethane gives mainly 1,4-dimethoxy-2-nitronaphthalene (1), 1,4-dimethoxy-2-trinitromethylnaphthalene (2) and 4-methoxy-2-(dinitromethylene)-1(2H)-naphthalenone (3) together with smaller amounts of the labile adducts 1,4-dimethoxy-2-trinitromethyl-1,2-dihydronaphthalen-1-ol (4), 1,4-dimethoxy-2-nitro-1-trinitromethyl-1,2-dihydronaphthalene (5) and 1,4-dimethoxy-1-nitro-2-trinitromethyl-1,2-dihydronaphthalene (6). Photolysis in acetonitrile gives higher yields of adducts 4 and 5. Photolysis in dichloromethane containing methanol gives mainly 1,1,4-trimethoxy-2-trinitromethyl-1,2-dihydronaphthalene (7) and 1,1,4-trimethoxy-2-nitro-1,2-dihydronaphthalene (8). Photolysis in acetonitrile containing methanol gives high yields of 8 and 4,4-dimethoxy-3-nitro-3,4-dihydro-1(2H)-naphthalenone (9). The formation of adducts via attack of trinitromethanide ion or nitrogen dioxide ipso to a methoxy group during the photolysis of 1,4-dimethoxynaphthalene and tetranitromethane is discussed, and arguments are presented that such adducts give compounds 2 and 3 via rearrangement and/or elimination reactions. The effect of methanol and the mode of formation of compounds 7-9 via nucleophilic addition or nucleophilic displacement are discussed. X-Ray crystallographic structures are reported for 1,4-dimethoxy-2-trinitromethylnaphthalene (2) and 4-methoxy-2-(dinitromethylene)-1(2H)-naphthalenone (3). Acta Chemica Scandinavica 1997.
NITRIC ACID ON SILICA GEL: A USEFUL NITRATING REAGENT FOR ACTIVATED AROMATIC COMPOUNDS
Tapia, Ricardo,Torres, Glenda,Valderrama, Jaime A.
, p. 681 - 688 (2007/10/02)
Phenols and arylmethyl ethers are rapidly mononitrated by nitric acid adsorbed in silica gel at room temperature in high yields.
