372199-85-4Relevant academic research and scientific papers
A novel approach for substitution of sulfonate group by (1H)-imidazole moiety: An application for synthesis of novel benzyl imidazolylcarbamates
Thripuram, Vijaya Durga,Bollikolla, Hari Babu,Mule, Siva Nagi Reddy,Battula, Sailaja Kumari,Ala, Vasu Babu
, p. 569 - 574 (2018/06/26)
An efficient and convenient substitution protocol was developed for the synthesis of novel benzyl (1-methyl-1H-imidazol-5-yl) (aryl) methyl carbamate derivatives from α-amido sulphones with a solution 5-bromo-1-methyl-(1H)-imidazole in THF under Hexamethy
An Efficient Copper-catalyzed Nucleophilic Addition to N-Acyliminium Ions Derived from N-Benzyloxycarbonylamino Sulfones: A Novel Approach to C-3 Functionalization of 2-Phenylimidazo[1,2-a]pyridine
Park, Hyeong Jin,Jun, Jong-Gab
, p. 1123 - 1128 (2017/09/19)
A general and efficient method for C-3 functionalization of 2-phenylimidazo[1,2-a]pyridine has been developed. The reaction employs Cu(OTf)2 as a catalyst at 10 mol% loading, proceeds in dimethyl sulfoxide solvent, and utilizes bench-stable sol
1-(N -acylamino)alkyl sulfones from N -acyl-α-amino acids or N -alkylamides
Adamek, Jakub,Mazurkiewicz, Roman,Pazdzierniok-Holewa, Agnieszka,Grymel, Miroslawa,Kuznik, Anna,Zielinska, Katarzyna
, p. 2765 - 2770 (2014/04/17)
A variety of N-(1-methoxyalkyl)amides or carbamates react readily with sodium aryl sulfinates in the presence of triphenylphosphonium tetrafluoroborate or bromide in CHCl3 under mild conditions to give 1-(N-acylamino)alkyl sulfones in good yiel
Leaving group and regioselectivity switches in the aminoalkylation reaction of indoles and related heterocycles with α-amido sulfones
Blay, Gonzalo,Giron, Rosa M.,Montesinos-Magraner, Marc,Pedro, Jose R.
supporting information, p. 3885 - 3895 (2013/07/19)
The regioselective aminoalkylation of indoles and related heterocycles with α-amido sulfones under basic conditions has been studied. The reaction that employed the MeMgBr/MgBr2 system provided high yields of 3-(1-carbamoylalkyl)indoles. On the other hand, the reaction that used Cs 2CO3 afforded 1-(1-carbamoylalkyl)indoles exclusively in high yields. The first reaction constitutes a switch of the leaving group of the α-amido sulfone in comparison to previously reported reactions between indoles and α-amido sulfones, which provided 3-(1-arylsulfonylalkyl) indoles. The second reaction constitutes a switch in the regioselectivity. The extensions of these C- and N-aminoalkylations starting from pyrroles and 7-azaindole have also been studied. Structurally diverse aminoalkylated indoles, pyrroles, and 7-azaindoles were obtained with excellent yield in most of the cases. The regioselective aminoalkylation of indoles and heterocycles with α-amido sulfones under basic conditions is described. The reaction with MeMgBr/MgBr2 gives 3-(1-carbamoylalkyl)indoles, whereas employing Cs2CO3 yields 1-(1-carbamoylalkyl)indoles. The first case presents a switch of the leaving group of the α-amido sulfone, whereas the second demonstrates a switch in the regioselectivity. Copyright
A mild and efficient catalytic mannich-type reaction as a simple access to N -benzyloxycarbonyl -amino ketones
Das, Biswanath,Reddy, Gandolla Chinna,Balasubramanyam, Penagaluri,Veeranjaneyulu, Boyapati
scheme or table, p. 2057 - 2062 (2010/08/13)
N-Benzyloxycarbonylamino sulfones react with aromatic ketones in the presence of catalytic amount of boron trifluoride-diethyl ether at room temperature to afford the corresponding protected β-amino ketones in high yields (71-87%). Georg Thieme Verlag Stu
Indium triflate-catalyzed allylation reactions of N-sulfonyl aldimines or N-alkoxycarbonylamino p-tolylsulfones with allyltrimethylsilane: Synthesis of protected homoallylic amines
Thirupathi, Ponnaboina,Kim, Sung Soo
scheme or table, p. 8623 - 8628 (2010/11/18)
Indium triflate-catalyzed allylation reactions of N-sulfonyl aldimines or N-alkoxyloxycarbonylamino p-tolylsulfone with allyltrimethylsilane have been successfully developed to produce protected homoallylic amines.
Asymmetric synthesis of maraviroc (UK-427,857)
Zhao, Gui-Ling,Lin, Shuangzheng,Korotvicka, Ales,Deiana, Luca,Kullberg, Martin,Cordova, Armando
supporting information; experimental part, p. 2291 - 2298 (2010/12/20)
The asymmetric synthesis of Maraviroc (UK-427,857), a chemochine receptor 5 (CCR-5) receptor antagonist, based on an expeditious organocatalytic enantioselective assembly of the chiral βamino aldehyde key fragment is presented. The reactions were performed on a gram-scale and allow for the rapid construction of new Maraviroc analogues.
InBr3: A versatile catalyst for the different types of Friedel-Crafts reactions
Thirupathi, Ponnaboina,Sung, Soo Kim
supporting information; experimental part, p. 7755 - 7761 (2009/12/27)
(Chemical Equation Presented) Mild and efficient InBr3-catalyzed Friedel-Crafts alkylation of heteroaromatic or electron-rich aromatic compounds with α-amido sulfones at room temperature in CH2Cl2 has been developed. The p
