7465-92-1Relevant academic research and scientific papers
Pd(OAc)2-catalyzed carbonylative coupling of aryl iodide with ortho-haloamines in water
Tambade, Pawan J.,Patil, Yogesh P.,Qureshi, Ziyauddin S.,Dhake, Kishor P.,Bhanage, Bhalchandra M.
supporting information; experimental part, p. 176 - 185 (2011/10/31)
The carbonylative cross coupling of aryl iodide with ortho-haloaniline to ortho-haloanilide using phosphine-free Pd(OAc)2 catalyst in water as a reaction medium has been studied. The present protocol facilitated the reaction of o-haloanilines with a wide variety of hindered and functionalized aryl iodides, affording good yields of the desired products. The protocol was also extended for the synthesis of benzoxazoles through cyclization of ortho-haloanilide using Cu(acac)2 catalyst. Taylor & Francis Group, LLC.
Synthesis and biological evaluation of a series of 2-(Substitutedphenyl) benzothiazoles
Nam, Nguyen Hai,Dung, Phan Thi Phuong,Thuong, Phuong Thien
, p. 127 - 134 (2013/01/10)
A series of 2-phenylbenzothiazoles has been synthesized either by i) condensation of different aromatic aldehydes with 2-aminothiophenol or ii) condensation of N-(2-chlorophenyl)benzothioamides in KOH catalyzed by potassium fericyanide. The structures of
Iron-catalyzed N-arylations of amides
Correa, Arkaitz,Elmore, Simon,Bolm, Carsten
experimental part, p. 3527 - 3529 (2009/04/11)
A method was proposed for iron-catalyzed N-arylation of primary amides and its applicability to the synthesis of N-heterocycles by intramolecular ring closures. The method used a catalyst system of 10 mol % of FeCl3 and 20 mol % of N,N'-dimethylethylenediamine (DMEDA). The study found that secondary amides of N-methylbenzamide and N-benzylbenzamide produce N-arylated products in trace amounts. The method developed an iron-based catalyst system for efficient N-arylations of primary amides with aryl iodides. The study used a sealable tube equipped with a magnetic stir bar charged with amide, or K 3PO4, or K2CO3, or FeCl3. The study used NMR spectroscopic analysis to determine the identity and purity of the products. The method observed that different substituted aryl iodides made a positive impact on the reaction.
The reaction of 2-chloro-4-nitrophenol and the isomeric chloronitrobenzenes with LDA under aryne-forming conditions
Tandel, Sagun,Wang, Anlai,Holdeman, Terra C.,Zhang, Hongming,Biehl, Edward R.
, p. 15147 - 15154 (2007/10/03)
The unprecedented base-initiated generation of a nitrobenzyne and subsequent addition of preformed arylacetonitrile anion nucleophiles is reported. In all cases, 2-amino-5-nitro-3-benzo[b]furans are obtained as major product with small amounts of 3-arylmethyl-2-cyano-4-nitrophenols. A mechanism involving ring closure of phenoxide and nitrile groups of the initial aryne-nitrile anion adduct is proposed to account for the formation of the benzofurans. The three isomeric chloronitrobenzynes, however, do not give aryne products when treated with LDA, but rather are reduced to the corresponding bis-dichloroazoxybenzenes.
Nitrile oxide-BF3 complex as electrophilic moiety towards aromatic systems: Stereospecific synthesis of oximes
Auricchio, Sergio,Bini, Antonella,Pastormerlo, Eros,Ricca, Aldo,Truscello, Ada M.
, p. 7589 - 7596 (2007/10/02)
Aromatic oximes are obtained stereospecifically by action of nitrile oxide-BF3 complexes on aromatic compounds.
Investigation of the Synthesis of Benzoxazole via Aryne Reaction
El-Sheikh, Mustafa I.,Marks, Alan,Biehl, Edward R.
, p. 3256 - 3259 (2007/10/02)
The reaction of o- and m-halobenzamides under aryne-forming conditions yielded the corresponding o-hydroxyphenyl amidines instead of the expected benzoxazole derivatives.The amidines, however, were converted to the corresponding benzoxazole either by sublimation or acidic hydrolysis.Evidence is presented that benzoxazoles are initially formed in these reactions but are readily aminated to the corresponding hydroxyphenyl amidines under the highly basic reaction conditions used in these aryne-forming reactions.
