13347-27-8Relevant academic research and scientific papers
Synthesis of Structurally Diverse Benzotriazoles via Rapid Diazotization and Intramolecular Cyclization of 1,2-Aryldiamines
Faggyas, Réka J.,Sloan, Nikki L.,Buijs, Ned,Sutherland, Andrew
supporting information, p. 5344 - 5353 (2019/05/21)
An operationally simple method has been developed for the preparation of N-unsubstituted benzotriazoles by diazotization and intramolecular cyclization of a wide range of 1,2-aryldiamines under mild conditions, using a polymer-supported nitrite reagent and p-tosic acid. The functional group tolerance of this approach was further demonstrated with effective activation and cyclization of N-alkyl, -aryl, and -acyl ortho-aminoanilines leading to the synthesis of N1-substituted benzotriazoles. The synthetic utility of this one-pot heterocyclization process was exemplified with the preparation of a number of biologically and medicinally important benzotriazole scaffolds, including an α-amino acid analogue.
Selenium-Catalyzed Carbonylative Synthesis of 2-Benzimidazolones from 2-Nitroanilines with TFBen as the CO Source
Qi, Xinxin,Zhou, Rong,Peng, Jin-Bao,Ying, Jun,Wu, Xiao-Feng
supporting information, p. 5161 - 5164 (2019/01/25)
A selenium-catalyzed carbonylative reaction for the synthesis of 2-benzimidazolones from 2-nitroanilines has been developed. In this strategy, to avoid the usage of toxic CO gas, TFBen (benzene-1,3,5-triyl triformate) was used as a solid and stable CO precursor, and a variety of desired 2-benzimidazolones were produced in moderate to excellent yields.
Microwave-assisted aza-Cope rearrangement of N-allylanilines
González, Israel,Bellas, Iria,Souto, Ana,Rodríguez, Ramón,Cruces, Jacobo
, p. 2002 - 2004 (2008/09/19)
The aza-Cope rearrangement of N-allylanilines is described. The use of BF3·OEt2 and microwave irradiation allows to run the transformation under mild conditions and in reaction times of minutes.
Palladium-catalyzed N-heteroannulation of N-allyl- or N-benzyl-2-nitrobenzenamines: synthesis of 2-substituted benzimidazoles
Hubbard, Jeremiah W.,Piegols, Adam M.,S?derberg, Bj?rn C.G.
, p. 7077 - 7085 (2008/02/10)
A palladium-catalyzed reductive N-heteroannulation of N-allyl- or N-benzyl-2-nitrobenzenamines, using carbon monoxide as the ultimate reducing agent, affording 2-substituted benzimidazoles has been developed.
Palladium-catalyzed allylation of acidic and less nucleophilic anilines using allylic alcohols directly
Hsu, Yi-Chun,Gan, Kim-Hong,Yang, Shyh-Chyun
, p. 1266 - 1269 (2007/10/03)
The direct activation of C-O bonds in allylic alcohols by palladium complexes has been accelerated by carrying out the reactions in the presence of titanium(IV) isoproxide and 4 A molecular sieves. The acidic and less nucleophilic anilines such as diphenylamine, phenothiazine, 4-cyanoaniline, and nitroanilines are efficiently allylated under palladium catalysis using allylic alcohols as allylating reagents.
An improved synthesis of N-substituted-2-nitroanilines
Chauhan,Singh, Ram,Geetanjali
, p. 2899 - 2906 (2007/10/03)
The reaction of 2-chloronitrobenzene with substituted amines/ anilines in the presence of DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) gives N-substituted-2-nitroanilines in good to excellent yields (>75-90%).
Synthesis of functionalised indolines by radical-polar crossover reactions
Murphy, John A.,Rasheed, Faiza,Gastaldi, Stephane,Ravishanker,Lewis, Norman
, p. 1549 - 1558 (2007/10/03)
Functionalised indolines have been prepared by treating tetrathiafulvalene (TTF) with 2-(N-acyl-N-allylamino)benzenediazonium tetrafluoroborates. N-Benzoyl-protected substrates afford complex reaction mixtures due to competing radical cyclisation onto the benzoyl group. Acetamides react more efficiently affording good yields of product alcohols when the reactions are carried out in moist acetone.
Boron trifluoride-diethyl ether complex catalyzed aromatic amino-Claisen rearrangements
Anderson,Lai
, p. 1287 - 1290 (2007/10/02)
Boron trifluoride-diethyl ether complex (BF3 · OEt2) was demonstrated to be an efficient catalyst for the amino-Claisen rearrangements of various aromatic N-allylamines into the corresponding o-allylamines in moderate yields.
The Stereochemistry of Organometallic Compounds. XL. Rhodium-Catalysed Reactions of Hydrogen and Carbon Monoxide with Alkenylanilines
Anastasiou, Despina,Campi, Eva M.,Chaouk, Hassan,Fallon, Gary D.,Jackson, W. Roy,et al.
, p. 1043 - 1060 (2007/10/02)
Rhodium-catalysed reactions of o- or p-cyano-N-allylanilines with H2/CO give N-arylpyrrolidine aldehydes resulting from a double hydroformylation sequence.In contrast reactions of o- or p-methyl-N-allylanilines or N-allylaniline itself with H2/CO give 'dimeric' compounds resulting from self-condensation reactions of an initially formed hydroformylation product together with varying amounts of the double hydroformylation product.Similar reactions of o-cyano-N-but-3-enylanilines give low yields of double hydroformylation products and major products arising from hydrogenation or cross coupling of intermediate enamines.The structure of one of these products, N-2-cyanophenyl-5-(N'-2-cyanophenyl-3-methylpyrrolidin-2-yl)-1,2,3,4-tetrahydropyridine (17) (IUPAC name: 2--1,2,3,4-tetrahydropyridin-1-yl>benzonitrile) was confirmed by an X-ray single-crystal structure determination.
A concise synthesis of a benzimidazole analogue of mycophenolic acid using a BF3-Et2O catalyzed amino-Claisen rearrangement
Lai,Anderson
, p. 6849 - 6852 (2007/10/02)
A nine-step synthesis of the benzimidazole analogue, 2, of mycophenolic acid is reported involving both the BF3-Et2O catalyzed aromatic amino- and the ortho ester Claisen rearrangements as key steps.
