3885-45-8Relevant academic research and scientific papers
Friedel-Crafts reaction of indoles with vicinal tricarbonyl compounds generated in situ from 1,3-dicarbonyl compounds and TEMPO: highly selective synthesis of tertiary alcohols
Yan, Jianwei,Ni, Tianjun,Yan, Fulin,Zhang, Jixia,Zhuang, Fangfang
, p. 89906 - 89910 (2015)
A novel Friedel-Crafts reaction of indoles with vicinal tricarbonyl compounds generated in situ from 1,3-dicarbonyl compounds, which produces indole substituted tertiary alcohols in good to excellent yields and with good functional group tolerance, has be
Structural insights into the desymmetrization of bulky 1,2-dicarbonyls through enzymatic monoreduction
Rabuffetti, Marco,Cannazza, Pietro,Contente, Martina Letizia,Pinto, Andrea,Romano, Diego,Hoyos, Pilar,Alcantara, Andres R.,Eberini, Ivano,Laurenzi, Tommaso,Gourlay, Louise,Di Pisa, Flavio,Molinari, Francesco
supporting information, (2021/01/25)
Benzil reductases are dehydrogenases preferentially active on aromatic 1,2-diketones, but the reasons for this peculiar substrate recognition have not yet been clarified. The benzil reductase (KRED1-Pglu) from the non-conventional yeast Pichia glucozyma showed excellent activity and stereoselectivity in the monoreduction of space-demanding aromatic 1,2-dicarbonyls, making this enzyme attractive as biocatalyst in organic chemistry. Structural insights into the stereoselective monoreduction of 1,2-diketones catalyzed by KRED1-Pglu were investigated starting from its 1.77 ? resolution crystal structure, followed by QM and classical calculations; this study allowed for the identification and characterization of the KRED1-Pglu reactive site. Once identified the recognition elements involved in the stereoselective desymmetrization of bulky 1,2-dicarbonyls mediated by KRED1-Pglu, a mechanism was proposed together with an in silico prediction of substrates reactivity.
Three-Component [2+2+1] Gold(I)-Catalyzed Oxidative Generation of Fully Substituted 1,3-Oxazoles Involving Internal Alkynes
Dubovtsev, Alexey Yu.,Dar'in, Dmitry V.,Kukushkin, Vadim Yu.
supporting information, p. 2926 - 2935 (2019/04/26)
Three-component [2+2+1] gold(I)-catalyzed reaction of internal alkynes (alkynyl esters or -ketones), nitriles, and 2-chloropyridine N-oxide led to a wide range of fully substituted 1,3-oxazoles (32 examples; up to 92% isolated yields). Nitrile R3/su
Rapid, Operationally Simple, and Metal-free NBS Mediated One-pot Synthesis of 1,2-Naphthoquinone from 2-Naphthol
Sim, Jaeuk,Jo, Hyeju,Viji, Mayavan,Choi, Minho,Jung, Jin-Ah,Lee, Heesoon,Jung, Jae-Kyung
supporting information, p. 852 - 858 (2018/02/06)
A metal-free, one-pot synthesis of 1,2-naphthoquinone was accomplished from 2-naphthol by utilizing economically cheap NBS under open air conditions. Initial formation of 1,1-dibromonaphthalen-2-one and subsequent transformation afforded the 1,2-naphthoquinone. This oxidation was completed within 30 min and had broad substrate scope. Moreover, this system tolerated heterocyclic systems and was also applicable to 1,3-dicarbonyl systems. This practical approach with short reaction times, a simple workup, and insensitivity to moisture could override the usage of expensive and hazardous oxidizing and metal reagents. (Figure presented.).
Displacement of Dinitrogen by Oxygen: A Methodology for the Catalytic Conversion of Diazocarbonyl Compounds to Ketocarbonyl Compounds by 2,6-Dichloropyridine-N-oxide
Yu, Yang,Sha, Qiang,Cui, Hui,Chandler, Kory S.,Doyle, Michael P.
supporting information, p. 776 - 779 (2018/02/09)
Dirhodium(II) catalyzed dinitrogen extrusion from diazocarbonyl compounds by 2,6-dichloropyridine-N-oxide forms ketocarbonyl compounds in near-quantitative yields. Reactions occur at room temperature, and the pyridine product does not coordinate with dirhodium(II) to inhibit catalysis. Anhydrous tricarbonyl compounds, as well as dicarbonyl compounds, are conveniently prepared by this methodology, and they have been used in situ for catalytic ene and aldol transformations.
Aerobic oxidation of β-dicarbonyls into vicinal tricarbonyls by Cu(II) salts for one-pot synthesis of quinoxalines
Han, Xu,Lei, Tao,Yang, Xiu-Long,Zhao, Lei-Min,Chen, Bin,Tung, Chen-Ho,Wu, Li-Zhu
supporting information, p. 1770 - 1774 (2017/04/13)
Vicinal tricarbonyl intermediates are directly synthesized from β-dicarbonyls with the aid of Cu(II) salts and air, and they are further condensed with phenylene diamine to produce a range of quinoxalines in moderate to good yields in one-pot reaction.
Oxidation of β-Ketoamides: The Synthesis of Vicinal Tricarbonyl Amides
Liu, Yueyang,Zhang, Zhiguo,Wan, Yameng,Zhang, Guisheng,Li, Zhonglian,Bi, Jingjing,Ma, Nana,Liu, Tongxin,Liu, Qingfeng
, p. 3901 - 3907 (2017/04/11)
A facile and direct oxidative reaction for the synthesis of vicinal tricarbonyl amides in moderate to excellent yields (53-88%) was developed starting from readily available β-ketoamides in the presence of phenyliodine(III) bis(trifluoroacetate). The resu
Synthesis and Photocatalytic Reactivity of Vinylsulfonium Ylides
Klose, Immo,Misale, Antonio,Maulide, Nuno
, p. 7201 - 7210 (2016/09/04)
Although sulfur ylides are textbook reagents in organic synthesis, surprisingly little variation of substituents on sulfur is usually observed. In particular, vinylsulfonium ylides have been neglected so far. Herein, we present a study on their synthesis and reactivity, including interesting behavior under photocatalytic conditions.
Lanthanide-catalyzed oxyfunctionalization of 1,3-diketones, acetoacetic esters, and malonates by oxidative C-O coupling with malonyl peroxides
Terent'ev, Alexander O.,Vil', Vera A.,Gorlov, Evgenii S.,Nikishin, Gennady I.,Pivnitsky, Kasimir K.,Adam, Waldemar
, p. 810 - 823 (2016/02/18)
The lanthanide-catalyzed oxidative C-O coupling of 1,3-dicarbonyl compounds with diacyl peroxides, specifically the cyclic malonyl peroxides, has been developed. An important feature of this new reaction concerns the advantageous role of the peroxide acti
Selectfluor-Mediated Simultaneous Cleavage of C-O and C-C Bonds in α,β-Epoxy Ketones under Transition-Metal-Free Conditions: A Route to 1,2-Diketones
Wang, Heng,Ren, Shaobo,Zhang, Jian,Zhang, Wei,Liu, Yunkui
, p. 6856 - 6863 (2015/10/06)
Selectfluor-mediated simultaneous cleavage of C-O and C-C bonds in α,β-epoxy ketones has been successfully achieved under transition-metal-free conditions. The reaction gives 1,2-diketone compounds in moderate to good yields involving a ring-opening/benzoyl rearrangement/C-C bond cleavage sequence under oxidative conditions.
