31913-94-7Relevant academic research and scientific papers
An efficient copper-catalyzed carbon-sulfur bond formation protocol in water
Ke, Fang,Qu, Yanyang,Jiang, Zhaoqiong,Li, Zhengkai,Wu, Di,Zhou, Xiangge
supporting information; experimental part, p. 454 - 457 (2011/04/15)
An efficient protocol of copper-catalyzed C-S bond formation between aryl halides and potassium thiocyanate leading to diaryl sulfides is reported. A variety of diaryl sulfides can be synthesized in good to excellent yields up to 94%.
Design, synthesis, enzyme inhibition, and tumor cell growth inhibition of 2-anilinobenzamide derivatives as SIRT1 inhibitors
Suzuki, Takayoshi,Imai, Keiko,Imai, Erika,Iida, Shinsuke,Ueda, Ryuzo,Tsumoto, Hiroki,Nakagawa, Hidehiko,Miyata, Naoki
experimental part, p. 5900 - 5905 (2009/12/24)
A series of 2-anilinobenzamide derivatives were designed, synthesized and evaluated for their SIRT1-inhibitory activity. Among these, compounds 3 and 5 inhibited SIRT1 activity in enzyme assays and suppressed the growth of Daudi and HCT116 cells.
Heteroatom-Directed Metalation. Lithiation of N-Propenylbenzamides and N-Propenyl-o-toluamides. Novel Routes to Ortho-Substituted Primary Benzamide Derivatives and N-Unsubstituted Isoquinolin-1(2H)-ones
Fisher, Lawrence E.,Muchowski, Joseph M.,Clark, Robin D.
, p. 2700 - 2705 (2007/10/02)
Reaction of N-propenylbenzamides 4 and 9, obtained by LDA-induced isomerization of the corresponding N-allylbenzamides, 1, 8, and 14, with 2 equiv of sec-butyllithium or tert-butyllithium at low temperature regiospecifically generates the highly reactive N,ortho-dilithiated species (e.g., 5 and 17).These dilithio species react avidly with a wide spectrum of electophilic reagents, including alky halides, giving adducts which on hydrolysis with warm 50percent aqueous acetic acid are converted into ortho-substituted primary benzamides in excellent yields.Ortho-lithiation of N-propenylbenzamides is thus formally equivalent to ortho-lithiation of primary benzamides themselves.The utility of this important, previously unknown, synthetic operation is enhanced by the well-known facility with which the primary amide moiety can be transformed into other useful functional groups, as exemplified by the synthesis of 2-methoxy-6-methylbenzoic acid (12) and 2-methoxy-6-methylbenzonitrile (13) from N-propenyl-2-methoxybenzamide (9).N-Propenyl-o-toluamide (7) undergoes regiospecific dilithiation on nitrogen and on the methyl group under conditions analogous to those used for the N-propenylbenzamides.These dilithio species react with DMF or "Weinreb type" amides to give condensation products which cyclize to N-propenylisoquinolin-1(2H)-ones under mildly acidic conditions.Removal of the N-propenyl moiety under more strongly acidic conditions provides N-unsubstituted isoquinolin-1(2H)-ones with high overall efficiency.This process is exemplified by the synthesis of isoquinolin-1(2H)-one (23) and its 3-n-butyl congener 26 from N-propenyl-2-methylbenzamide (7).
SYNTHESIS OF (2-(PHENYLTHIO)PHENYL)ACETAMIDINES AND RELATED AMIDOXIMES AS POTENTIAL ANTIDEPRESSANTS
Sindelar, Karel,Sedivy, Zdenek,Hrubantova, Marta,Valchar, Martin,Metysova, Jirina,Protiva, Miroslav
, p. 381 - 388 (2007/10/02)
Reactions of ethyl (2-(phenylthio)phenyl)acetimidate (X) hydrochloride with ammonia and the corresponding amines resulted in amidines V-X.Heating (2-(phenylthio)phenyl)acetonitrile with 2-aminoethylammonium toluene-4-sulfonate led to the 2-imidazoline XI.
PHOTOCHEMISTRY OF HYDROXAMIC ACIDS
Hosangadi, B.D.,Chhaya, P.N.,Nimbalkar, M.M.,Patel, N.R.
, p. 5375 - 5380 (2007/10/02)
Photochemical reactions of hydroxamic acids have been studied.The intermediacy of a RCONH(.) radical is postulated, based on oxidations achieved with DCA under photochemical conditions.
Acid-Catalyzed Reactions of Ortho-Substituted Benzohydroxamic Acids in Polyphosphoric Acid (PPA)
Chhaya, P. N.,Nimbalkar, M. M.,Hosangadi, B. D.
, p. 4458 - 4460 (2007/10/02)
Ortho-substituted benzohydroxamic acids undergo a variety of reactions when treated with PPA.The nature of substituents on the ring and on the functional group CONHOH plays a key role in influencing the reaction pathways.The difference in behavior may arise due to change in site of protonation depending upon the substitution.However, no clear-cut relationship could be established as attempts to monitor reactions on NMR proved inconclusive.
PHOTOCHEMICAL REACTIONS OF BENZOHYDROXAMIC ACIDS
Chhaya, Pradeep,Nimbalkar, Manmohan,Hosangadi, Bhaskar
, p. 5551 - 5552 (2007/10/02)
2-(Arylthio)benzohydroxamic acids 1 and 2 undergo photodeoxygenation under unsensitised irradiations.DCA sensitized irradiation of a model benzohydroxamic acid (5), however, yields 1,2-diacyldiazine (6).
Studies in Rearrangement of 2-(Arylthio)benzohydroxamic Acids to the Corresponding 2-(Arylsulphinyl)benzamides
Dhareshwar, G. P.,Chhaya, P. N.,Hosangadi, B. D.
, p. 831 - 835 (2007/10/02)
2-(2'-Methoxyphenylthio)-(III)-, 2-(4'-methoxyphenylthio)-(IV)-, 2-(2'-methylphenylthio)-(V)- and 2-(4'-methylphenylthio)-(VI)-benzohydroxamic acids on treatment with polyphosphoric acid yield 2-(2'-methoxyphenylsulphinyl)-(VII)-, 2-(4'-methoxyphenylsulphinyl)-(VIII)-, 2-(2'-methylphenylsulphinyl)-(IX)- and 2-(4'-methylphenylsulphinyl)-(X)-benzamides respectively, illustrating the generality of rearrangement reported earlier .The rearrangement can also be effected with other reagents like xylene-P2O5, perchloric acid- gl. acetic acid and trifluoracetic acid. 2-Methylthiobenzohydroxamic acid (XI) and 4-(phenylthio)benzohydroxamic acid (XII) when treated with PPA yield benzothiazolone (XIII) and 4-aminodiphenyl sulphide (XIV).Experimental evidence has been presented which points to a concerted mechanism for the intramolecular oxygen transfer.
Phenylthioaralkylamines
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, (2008/06/13)
Phenylthioaralkylamines and 2-phenylthiobenzylamines are prepared by reaction of the corresponding phenylthiobenzoyl chloride or homologs thereof with ammonia or an amine to produce the corresponding phenylthiobenzamide or N-substituted or N,N-disubstitut
