79229-99-5Relevant academic research and scientific papers
Copper(ii)-catalyzed synthesis of multisubstituted indoles through sequential Chan-Lam and cross-dehydrogenative coupling reactions
Bian, Yunyun,Chen, Chunxia,Chen, Xin,Mo, Baichuan,Peng, Jinsong,Sun, Peng
, p. 24830 - 24839 (2020/07/14)
Starting from arylboronic acids and ester (Z)-3-aminoacrylates, one-pot syntheses of diverse indole-3-carboxylic esters have been described through copper(ii)-catalyzed sequential Chan-Lam N-arylation and cross-dehydrogenative coupling (CDC) reactions. The initial Chan-Lam arylation can proceed in DMF at 100 °C for 24 h to give ester (Z)-3-(arylamino)acrylate intermediates in the presence of Cu(OAc)2/tri-tert-butylphosphine tetrafluoroborate, a catalytic amount of myristic acid as the additive, KMnO4 and KHCO3. Sequentially, these in situ arylated intermediates can undergo an intramolecular oxidative cross-dehydrogenative coupling process in mixed solvents (DMF/DMSO = 2 : 1) at 130 °C to give C3-functionalized multi-substituted indole derivatives. This journal is
Solid Supported Chiral N-Picolylimidazolidinones: Recyclable Catalysts for the Enantioselective, Metal- and Hydrogen-Free Reduction of Imines in Batch and in Flow Mode
Porta, Riccardo,Benaglia, Maurizio,Annunziata, Rita,Puglisi, Alessandra,Celentano, Giuseppe
supporting information, p. 2375 - 2382 (2017/07/22)
A new class of solid supported chiral imidazolidinone organocatalysts for the catalytic reduction of imines with trichlorosilane has been developed. Polystyrene proved to be a more effective support than silica in terms of both chemical and stereochemical
HOTf-catalyzed intermolecular hydroamination reactions of alkenes and alkynes with anilines
Xu, Xuefeng,Zhang, Xu,Wang, Zhiqiang,Kong, Manman
, p. 40950 - 40952 (2015/05/20)
Herein, the intermolecular hydroamination of alkenes and alkynes with anilines catalyzed by HOTf under mild conditions has been developed. This reaction provides one of the simplest alkene and alkyne addition methods and is an alternative to metal-catalyzed reactions. At the same time, the intramolecular hydroamination of alkynes with anilines proceeds smoothly to obtain quinolines. We found that this strategy is efficient in building complex structures from simple starting materials in an environmentally benign fashion.
Cinchona-Derived Picolinamides: Effective Organocatalysts for Stereoselective Imine Hydrosilylation
Barrulas, Pedro C.,Genoni, Andrea,Benaglia, Maurizio,Burke, Anthony J.
supporting information, p. 7339 - 7342 (2016/02/20)
Picolinamide-cinchona organocatalysts for the successful enantioselective reduction of ketomines were developed. For the first time, a new type of chiral Lewis base, a cationic species, is reported to efficiently organocatalyze the addition of trichlorosi
Synthesis of diversely substituted indoloquinolinones via Pd(II)/Cu(II)-mediated oxidative C-C bond formation and I(III)-mediated C-N bond formation
Zhang, Xiang,Zhang-Negrerie, Daisy,Deng, Jun,Du, Yunfei,Zhao, Kang
, p. 12750 - 12759 (2014/01/17)
A series of indoloquinolinones bearing different aromatic substitutents were readily synthesized starting from an aryl amine, a methyl 3-oxo-3-phenylpropanoate derivative, and methoxylamine through a series of reactions of coupling/enamination, oxidative
Highly regioselective AgNTf2-catalyzed intermolecular hydroamination of alkynes with anilines
Zhang, Xu,Yang, Bin,Li, Guangzhao,Shu, Xin,Mungra, Divyesh C.,Zhu, Jin
supporting information; experimental part, p. 622 - 626 (2012/04/04)
A facile and economic method for the fully regioselective and high-yielding protocol for the hydroamination of unsymmetrical internal alkynes under mild reaction conditions with AgNTf2 was developed. The materials are easily available from comm
Highly enantioselective synthesis of β-amino acid derivatives by the lewis base catalyzed hydrosilylation of β-enamino esters
Zheng, Hong-Jie,Chen, Wen-Bing,Wu, Zhi-Jun,Deng, Jin-Gen,Lin, Wen-Qing,Yuan, Wei-Cheng,Zhang, Xiao-Mei
, p. 9864 - 9867 (2009/10/02)
A study was conducted to demonstrate highly enantioselective synthesis of β-amino acid derivatives by the Lewis base catalyzed hydrosilylation of βenamino esters. It was found that these catalyst and its analogue displayed excellent activities and enantioselectivities in promoting hydrosilylation of N-aryl β-enamino esters. N-picolinoylpyrrolidine derivatives and N-picolioylephedrine were also evaluated in hydrosilylation of (Z)-methyl 3-phenyl-3-(phenylamino)acrylate. The generality of the Lewis base organocatalyzed hydrosilylation of various β-enamino esters were examined under the optimized conditions. It was observed that the catalytic system exhibited a high sensitivity to the N-substituents, while all the N-aryl β-enamino esters underwent the hydrosilylation smoothly to give corresponding β-amino esters.
REACTIONS OF METHYL 3-ARYL-2-PROPYONATES WITH NUCLEOPHILIC NITROGEN COMPOUNDS
Moussa, G. E. M.,Basyouni, M. N.,Fouli, F. A.,Kandeel, K. A.
, p. 167 - 174 (2007/10/02)
Benzylamine reacts with methyl 3-phenyl-(IVa) and methyl 3-(p-methoxyphenyl)-(IVb)2-propynoates to give the corresponding N-benzyl-3-aryl-2-propynoic amides (Va and b).On the other hand, methyl 3-(p-chlorophenyl)-2-propynoate (IVc) give methyl (Z)-β-benzylamino-p-chlorocinnamate (VIa). p-Methylaminobenzene and p-methoxyaminobenzene react with IVa-c to give the corresponding methyl (Z)-β-(arylamino)cinnamates (VIb-g).Similarly, o-phenylenediamine gave with IVc, methyl (Z)-β-(o-aminoanilino)-p-chlorocinnamate (VII).Benzoylhydrazine reacts with IVa and b to give the corresponding 1H-3-aryl-1-benzoyl-5-hydroxypyrazole (VIIIa and b); VIIIa was converted into the known 3-phenylpyrazol-5-one by the action of concentrated hydrochloric acid.Benzamidine hydrochloride and IVa-c in the presence of aqueous sodium carbonate give the correesponding methyl (Z)-β-benzamidinocinnamates (IXa-c).
