195191-58-3Relevant articles and documents
Yeast supported gold nanoparticles: an efficient catalyst for the synthesis of commercially important aryl amines
Krishnan, Saravanan,Patel, Paresh N.,Balasubramanian, Kalpattu K.,Chadha, Anju
supporting information, p. 1915 - 1923 (2021/02/06)
Candida parapsilosisATCC 7330 supported gold nanoparticles (CpGNP), prepared by a simple and green method can selectively reduce nitroarenes and substituted nitroarenes with different functional groups like halides (-F, -Cl, -Br), olefins, esters and nitriles using sodium borohydride. The product aryl amines which are useful for the preparation of pharmaceuticals, polymers and agrochemicals were obtained in good yields (up to >95%) using CpGNP catalyst under mild conditions. The catalyst showed high recyclability (≥10 cycles) and is a robust free flowing powder, stored and used after eight months without any loss in catalytic activity.
Coupling N-H Deprotonation, C-H Activation, and Oxidation: Metal-Free C(sp3)-H Aminations with Unprotected Anilines
Evoniuk, Christopher J.,Gomes, Gabriel Dos Passos,Hill, Sean P.,Fujita, Satoshi,Hanson, Kenneth,Alabugin, Igor V.
supporting information, p. 16210 - 16221 (2017/11/22)
An intramolecular oxidative C(sp3)-H amination from unprotected anilines and C(sp3)-H bonds readily occurs under mild conditions using t-BuOK, molecular oxygen and N,N-dimethylformamide (DMF). Success of this process, which requires mildly acidic N-H bonds and an activated C(sp3)-H bond (BDE 85 kcal/mol), stems from synergy between basic, radical, and oxidizing species working together to promote a coordinated sequence of deprotonation: H atom transfer and oxidation that forges a new C-N bond. This process is applicable for the synthesis of a wide variety of N-heterocycles, ranging from small molecules to extended aromatics without the need for transition metals or strong oxidants. Computational results reveal the mechanistic details and energy landscape for the sequence of individual steps that comprise this reaction cascade. The importance of base in this process stems from the much greater acidity of transition state and product for the 2c,3e C-N bond formation relative to the reactant. In this scenario, selective deprotonation provides the driving force for the process.
N-heterocyclic carbene-catalyzed conjugate umpolung for the synthesis of γ-butyrolactones
Burstein, Christian,Tschan, Serena,Xie, Xiulan,Glorius, Frank
, p. 2418 - 2439 (2008/03/13)
The N-heterocyclic carbene-catalyzed conjugate Umpolung of differently substituted α,β-unsaturated aldehydes, e. g. cinnamaldehydes, α-methylcinnamaldehydes, and crotonaldehydes, is described. Coupling of these compounds with a variety of electrophilic al
Facile synthesis of biologically active heterocycles by indium-induced reactions of aromatic nitro compounds in aqueous ethanol
Banik, Bimal K.,Banik, Indrani,Samajdar, Susanta,Wilson, Mary
, p. 283 - 296 (2007/10/03)
Indium/ammonium chloride-induced reduction of aromatic nitro compounds to aromatic amines in aqueous ethanol was developed. Useful chemoselectivity was observed in the reduction reaction. This method was extended to reductive cyclization and rearrangement toward the synthesis of various biologically active heterocycles, including quinoline, oxazines, quinalonones, and phenanthridine in excellent yield. The oxophilicity of indium metal influenced the reaction in aqueous ethanol. Metals like zinc and tin were not effective in promoting this kind of reactions under the present environmentally friendly conditions.
Indium-mediated reductive cyclizations in aqueous ethanol: Highly efficient synthesis of heterocyclic compounds of biological interests
Banik, Bimal K.,Banik, Indrani,Hackfeld, Linda,Becker, Frederick F.
, p. 467 - 470 (2007/10/03)
Indium/ammonium chloride in the presence of aqueous ethanol was found to be very effective in reductive cyclization reactions leading to the development of several heterocyclic compounds of biological significance.
Intramolecular Michael-type addition of azadienes to 1,4-naphthoquinones instead of Aza-Diels-Alder cycloaddition: A synthesis of ascididemin
Cuerva, Juan M.,Cardenas, Diego J.,Echavarren, Antonio M.
, p. 1360 - 1365 (2007/10/03)
α,β-Unsaturated hydrazones tethered by an amino group to 1,4-naphthoquinone or quinoline-5,8-dione do not react by intramolecular aza-Diels-Alder cycloaddition. Instead, these substrates cyclize to form benzo[b]acridine-6,11-dione or pyrido[2,3-b]acridine-5,12-dione derivatives, respectively. This route leads to a highly concise synthesis of the pyridoacridine alkaloid ascididemin.
