76854-95-0Relevant academic research and scientific papers
Direct Hydroxylation and Amination of Arenes via Deprotonative Cupration
Tezuka, Noriyuki,Shimojo, Kohei,Hirano, Keiichi,Komagawa, Shinsuke,Yoshida, Kengo,Wang, Chao,Miyamoto, Kazunori,Saito, Tatsuo,Takita, Ryo,Uchiyama, Masanobu
supporting information, p. 9166 - 9171 (2016/08/05)
Deprotonative directed ortho cupration of aromatic/heteroaromatic C-H bond and subsequent oxidation with t-BuOOH furnished functionalized phenols in high yields with high regio- and chemoselectivity. DFT calculations revealed that this hydroxylation reaction proceeds via a copper (I → III → I) redox mechanism. Application of this reaction to aromatic C-H amination using BnONH2 efficiently afforded the corresponding primary anilines. These reactions show broad scope and good functional group compatibility. Catalytic versions of these transformations are also demonstrated.
Beyond directed ortho metalation: Ruthenium-catalyzed amide-directed C Ar-N activation/C-C coupling reaction of anthranilamides with organoboronates
Zhao, Yigang,Snieckus, Victor
supporting information, p. 3200 - 3203 (2014/07/08)
A new, catalytic, and general methodology for the synthesis of biaryls and heterobiaryls by the cross coupling of anthranilamide derivatives (o-NMe 2 benzamides) with aryl boroneopentylates is described. The reaction proceeds under catalytic RuH2(CO)(PPh3)3 conditions driven by the activation of the unreactive C-N bond by amide directing group (DG)-Ru catalyst chelation. High regioselectivity, orthogonality with the Suzuki-Miyaura reaction, operational simplicity, and convenient scale-up are features of these reactions which may lend themselves to industrial applications.
Synthesis, antimicrobial evaluation, ot-QSAR and mt-QSAR studies of 2-amino benzoic acid derivatives
Mahiwal, Kuldeep,Kumar, Pradeep,Narasimhan, Balasubramanian
experimental part, p. 293 - 307 (2012/09/07)
A series of 2-amino benzoic acid derivatives (1-28) were synthesized and evaluated for their in vitro antimicrobial activity against the panel of Gram positive, Gram negative bacterial and fungal strains. The results of antimicrobial studies indicated that, in general, the synthesized compounds were found to be bacteriostatic and fungistatic in action. QSAR studies performed by the development of one target and multi target models indicated that multi-target model was effective in describing the antimicrobial activity as well demonstrated the effect of structural parameters viz. LUMO, 3χv and W on antimicrobial activity of 2-amino benzoic acid derivatives. Springer Science+Business Media, LLC 2010.
Synthesis of 2-hydroxy-3-indolinones and 3-hydroxy-2-indolinones by anionic cyclization, in situ oxidation and rearrangement
Coldham, Iain,Adams, Harry,Ashweek, Neil J.,Barker, Thomas A.,Reeder, Andrew T.,Skilbeck, Melanie C.
scheme or table, p. 2457 - 2460 (2010/07/04)
Lithiation with butyllithium of 2-(benzylamino)benzamides (N-benzyl anthranilamides) occurs at the benzylic position to give an α-amino-organolithium that cyclizes to the 3-indolinone (indoxyl) ring (similar to a Parham cyclization). Autoxidation in air g
Design, synthesis and biological evaluation of substituted dioxodibenzothiazepines and dibenzocycloheptanes as farnesyltransferase inhibitors
Gilleron, Pauline,Wlodarczyk, Nicolas,Houssin, Raymond,Farce, Amaury,Laconde, Guillaume,Goossens, Jean-Francois,Lemoine, Amelie,Pommery, Nicole,Henichart, Jean-Pierre,Millet, Regis
, p. 5465 - 5471 (2008/03/11)
A new series of FTase inhibitors containing a tricyclic moiety-dioxodibenzothiazepine or dibenzocycloheptane-has been designed and synthesized. Among them, dioxodibenzothiazepine 18d displayed significant inhibitory FTase activity (IC50 = 17.3
Imidazoline derivatives as alpha-1A adrenoceptor ligands
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Page/Page column 19, (2010/02/11)
Compound of formula (I) or a pharmaceutically acceptable salt or solvate thereof are disclosed. Such compounds are useful in the treatment of Alpha-1A mediated diseases or conditions such as urinary incontinence.
Conjugate additions of o-iodoanilines and methyl anthranilates to acetylenic sulfones. A new route to quinolones including first syntheses of two alkaloids from the medicinal herb Ruta chalepensis
Back, Thomas G.,Parvez, Masood,Wulff, Jeremy E.
, p. 2223 - 2233 (2007/10/03)
A novel synthesis of 2-substituted 4-quinolones was developed on the basis of the conjugate additions of appropriately ortho-substituted anilines to acetylenic sulfones followed by intramolecular acylation of the corresponding sulfone-stabilized anions. C
New approach to biomimetic transamination using bifunctional [1,3]-proton transfer catalysis in thioxanthenyl dioxide imines
Hjelmencrantz, Anders,Berg, Ulf
, p. 3585 - 3594 (2007/10/03)
A pyridoxamine equivalent, 9-aminothioxanthene 10,10-dioxide, has been designed that is capable of affording transamination in good to excellent yields of natural as well as artificial amino acids. Amidines and guanidines in catalytic amounts were capable of performing [1,3]-proton transfer in the imines under mild conditions, whereas various simple amines failed. The use of chiral catalysts resulted in modest asymmetric induction (ee ≤ 45%). The electronic dependence in para-substituted phenyl glyoxylate imines, isotope effects, and computational studies support a stepwise, bifunctional mechanism for amidine and guanidine catalysts. Attempts toward an autocatalytic model system are described.
Novel dibenzothiazepines without substitution on the sulfonamide group
Lebegue, Nicolas,Flouquet, Nathalie,Berthelot, Pascal,Pfeiffer, Bruno,Renard, Pierre
, p. 2877 - 2884 (2007/10/03)
We have developed the synthesis of new thiazepine compounds bearing a non substituted sulfonamide group, which is described through two different synthetic pathways, to design new anticancer structural families.
A laser flash photolysis study on 2-azido-N,N-diethylbenzylamine - The reactivity of iminoquinone methides in solution
Bucher, Goetz
, p. 2463 - 2475 (2007/10/03)
Photolysis of 2-azido-N,N-diethylbenzylamine (1) in acetonitrile solution in the presence of various quenchers yields products of common nitrene chemistry (that is, derived from a didehydroazepine or a triplet nitrene), together with products arising from trapping of stereoisomeric iminoquinone methides. These intermediates are formed in a monophotonic process, by dediazotation of the precursor combined with a 1,4-hydrogen shift. The reactivity of the iminoquinone methides (IQM) towards a variety of quenchers, including dienophiles and various nucleophiles, has been explored, using acetonitrile, DMF, and n-hexane as solvents. IQM reacts efficiently with electron deficient dienophiles [kq(maleic anhydride) = 2.4·107 M-1 s-1], but not with simple olefins such as cyclohexene. IQM shows low to medium reactivity towards simple primary or secondary amines [kq(n-propylamine) = 6.4·104 M-1 s-1], medium reactivity with sterically unhindered simple alcohols [kq(methanol) = 4.6·106 M-1 s-1], and high to very high reactivity towards thiols [kq(n-dodecanethiol) = 1.1·109 M-1 s-1], diols, and triols [kq(glycerol) = 1.5·108 M-1 s-1], and sugars [kq(D-glucose) = 1.0·109 M-1 s-1]. IQM also reacts rapidly with cytosine: kq(cytosine) = 3.4·108 M-1 s-1, while the reaction with adenine or thymine is less efficient [kq(adenine) = 6.4·107 M-1 s-1, kq(thymine) = 7.7·106 M-1 s-1].
