24246-87-5Relevant academic research and scientific papers
A facile transformation of alkynes into α-amino ketones by an N-bromosuccinimide-mediated one-pot strategy
Wei, Ting,Zeng, Yongming,He, Wei,Geng, Lili,Hong, Liang
, p. 383 - 385 (2018/04/11)
A facile transformation of alkynes into α-amino ketones by an N-bromosuccinimide-mediated one-pot cascade strategy is described. A variety of α-amino ketones are obtained in moderate to good yields under mild conditions. To overcome the multi-step synthesis, N-bromosuccinimide is involved in multiple tasks, playing a key role in the reaction course.
A METAL FREE PROCESS FOR THE PREPARATION OF ALPHA-SUBSTITUTED CARBONYL COMPOUNDS FROM ALKENES
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Page/Page column 15-16, (2017/06/19)
The present invention discloses a novel metal free process for the regioselective synthesis of α-substituted carbonyl compounds of formula I from alkene, X is selected from the following compounds (A, B).
Regioselective oxo-amination of alkenes and enol ethers with N-bromosuccinimide-dimethyl sulfoxide combination: A facile synthesis of α-amino-ketones and esters
Prasad, Pragati K.,Reddi, Rambabu N.,Sudalai, Arumugam
, p. 500 - 503 (2016/02/18)
An unprecedented conversion of alkenes and enol ethers to the corresponding α-imido carbonyl compounds with excellent regioselectivity and yields has been developed. This oxo-amination process employs readily available N-bromosuccinimide (NBS) and secondary amines as N-sources and dimethyl sulfoxide (DMSO) as the oxidant and also leads to the production of amino alcohols in a single step on reduction, thus broadening the scope of this operationally simple reaction. For the first time, the formation of reactive Me2S+-O-Br species generated by the interaction of NBS with DMSO has been proven.
N-Bromosuccinimide promoted and base switchable one pot synthesis of α-imido and α-amino ketones from styrenes
Shinde, Mahesh H.,Kshirsagar, Umesh A.
supporting information, p. 858 - 861 (2016/01/15)
An N-Bromosuccinimide (NBS) promoted one pot strategy for the synthesis of α-amino functionalized aryl ketones starting from commercially available styrenes has been developed. NBS participates in multiple tasks, such as bromonium ion formation, oxidation of bromohydrin and providing a nucleophilic nitrogen source. The reaction can easily be switched between α-imido and α-amino ketones by the choice of base. This one pot strategy was successfully applied for the synthesis of psychoactive drug candidates, amfepramone, mephedrone and 4-MEC.
N-Heterocyclic Carbene Catalyzed Oxidative Coupling of Alkenes/ α-Bromoacetophenones with Aldehydes: A Facile Entry to α,β-Epoxy Ketones
Reddi, Rambabu N.,Prasad, Pragati K.,Sudalai, Arumugam
supporting information, p. 14150 - 14153 (2016/01/25)
A novel, N-heterocyclic carbene (NHC) catalyzed direct oxidative coupling of styrenes with aldehydes has been described for the synthesis of α,β-epoxy ketones in good yields. This unprecedented regioselective oxidative coupling employs NBS/DBU/DMSO (DBU=1,8-diazabicyclo [5.4. 0] undec-7-ene, DMSO=dimethylsulfoxide, NBS=N-bromosuccinimide) as an oxidative system at ambient conditions. Additionally, first NHC-catalyzed Darzens reaction of α-bromoketones and aldehydes under mild reaction conditions has also been described. Interestingly, mechanistic studies have revealed the preferred reactivity of NHC with alkene/α-bromoketone rather than aldehydes, thus proceeding via the ketodeoxy Breslow intermediate.
Ag-and Au-catalyzed addition of alcohols to ynimides: β-regioselective carbonylation and production of oxazoles
Sueda, Takuya,Kawada, Arisa,Urashi, Yumi,Teno, Naoki
supporting information, p. 1560 - 1563 (2013/06/26)
Metal-catalyzed reactions of ynimides with alcohols to afford β-ketoimides and oxazoles are demonstrated. The triple bond of ynamides is generally activated by mineral acids or metal salts to lead to the regioselective addition of nucleophiles at the α-C-
One-pot cascade leading to direct α-imidation of ketones by a combination of N-bromosuccinimide and 1,8-diazabicyclo[5.4.1]undec-7-ene
Wei, Ying,Lin, Shaoxia,Liang, Fushun
experimental part, p. 4202 - 4205 (2012/10/08)
A one-pot cascade transformation of ketones into α-imidoketones has been developed, in which N-bromosuccinimide (NBS) provides both electrophilic bromine and nucleophilic nitrogen sources, and diazabicyclo[5.4.1]undec-7-ene (DBU) functions as a base and a
1,3-Dioxolane-based ligands incorporating a lactam or imide moiety: Structure-affinity/activity relationship at α1-adrenoceptor subtypes and at 5-HT1A receptors
Franchini, Silvia,Prandi, Adolfo,Baraldi, Annamaria,Sorbi, Claudia,Tait, Annalisa,Buccioni, Michela,Marucci, Gabriella,Cilia, Antonio,Pirona, Lorenza,Fossa, Paola,Cichero, Elena,Brasili, Livio
experimental part, p. 3740 - 3751 (2010/11/18)
A series of 1,3-dioxolane-based compounds incorporating a lactam (2-4) or imide (5-7) moiety was synthesized and the pharmacological profile at α1-adrenoceptor subtypes and 5-HT1A receptor was assessed through binding and functional experiments. Starting from the 2,2-diphenyl-1,3-dioxolane derivative 1, previously shown to be a selective α1a(A)/α1d(D)-adrenoceptor subtype antagonist, over α1b(B) subtype and 5-HT1A receptor, and replacing one phenyl ring with lactam or imide moiety a reduction of α1/5-HT1A selectivity is observed, mainly due to the increase in 5-HT1A affinity. In functional experiments lactam derivatives seems to favour 5-HT1A receptor antagonism (pKb = 7.20-7.80) and α1B-adrenoceptor antagonist selectivity (α1B/α1A and α1B/ α1D of about 10-fold). The most interesting of the various imide derivatives is compound 7t, which is a selective α1D- adrenoceptor antagonist (pKb = 8.1 and α1D/α1A and α1D/α1B selectivity ratios of 16 and 11 respectively) whereas at 5-HT1A receptor it is a potent partial agonist (pD2 = 7.98, Emax = 60%).]. Given that cis and trans diastereomer pairs for 2-7 are possible, a computational strategy based on molecular docking studies was used to elucidate the atomic details of the 5HT1A/agonist and 5HT1A/antagonist interaction. The lactam derivatives seems to favour 5-HT1A receptor antagonism and α1B-adrenoceptor antagonist selectivity. The imide derivative 7t is a selective α1D-adrenoceptor antagonist whereas at 5-HT1A receptor it is a potent partial agonist.
Formal synthesis of salinosporamide A via NHC-catalyzed intramolecular lactonization
Struble, Justin R.,Bode, Jeffrey W.
experimental part, p. 4957 - 4967 (2009/11/30)
An N-heterocyclic carbene (NHC) catalyzed intramolecular lactonization to prepare densely functionalized bicyclic γ-lactam-γ-lactone adducts from enals is reported. This method has been applied to the formal synthesis of salinosporamide A, a potent 20S pr
Two efficient enantioselective syntheses of 2-amino-1-phenylethanol
Tanielyan, Setrak K.,Marin, Norman,Alvez, Gabriela,Augustine, Robert L.
, p. 893 - 898 (2012/12/23)
Two enantioselective methods for the synthesis of 2-amino-1-phenylethanol have been developed. The first utilizes an enantioselective oxazaborolidine- catalyzed borane reduction of 2-chloroacetophenone (phenacyl chloride) to give the chiral chloro alcohol in good yield with an ee in the 93-97% range. Reaction with dilute ammonium hydroxide produced the amino alcohol in good yield with a high ee. The second approach involved first the conversion of phenacyl chloride to the succinimido acetophenone which was then hydrogenated using a chiral ruthenium complex in conjunction with a base and an optically active amine (Noyori procedure). This gave the optically active succinimido alcohol in very good yield with an ee of 98%. Hydrolysis with dilute base produced the optically active amino alcohol in very good yield and excellent enantioselectivity.
