3432-87-9Relevant academic research and scientific papers
I-Pr2NMgCl·LiCl Enables the Synthesis of Ketones by Direct Addition of Grignard Reagents to Carboxylate Anions
Colas, Kilian,Dos Santos, A. Catarina V. D.,Mendoza, Abraham
supporting information, (2019/10/08)
The direct preparation of ketones from carboxylate anions is greatly limited by the required use of organolithium reagents or activated acyl sources that need to be independently prepared. Herein, a specific magnesium amide additive is used to activate and control the addition of more tolerant Grignard reagents to carboxylate anions. This strategy enables the modular synthesis of ketones from CO2 and the preparation of isotopically labeled pharmaceutical building blocks in a single operation.
Gold-catalyzed cyclization of 1-(2′-Azidoaryl) propynols: Synthesis of polysubstituted 4-quinolones
Wu, Xiang,Zheng, Lang-Lang,Zhao, Li-Ping,Zhu, Cheng-Feng,Li, You-Gui
supporting information, p. 14769 - 14772 (2019/12/24)
An unprecedented gold-catalyzed procedure for the synthesis of polysubstituted 4-quinolones from 1-(2′-Azidoaryl) propynols is described. The reaction undergoes an intramolecular nucleophilic attack of the azide group to the Au-Activated triple bonds in a 6-endo-dig manner and subsequent gold-Assisted expulsion of N2 to furnish an α-imino gold carbene intermediate, which triggers a 1,2-carbon migration and finally is converted to 2,3-disubstituted 4-quinolone.
Catalyst-free geminal aminofluorination of ortho-sulfonamide-tethered alkylidenecyclopropanes via a Wagner-Meerwein rearrangement
Fan, Xing,Wang, Qiang,Wei, Yin,Shi, Min
supporting information, p. 10503 - 10506 (2018/09/21)
A catalyst-free intramolecular geminal aminofluorination of ortho-sulfonamide-tethered alkylidenecyclopropanes has been developed. The reaction proceeded through two SET processes with Selectfluor to give a fluorinated cyclopropylcarbinyl cation and a further Wagner-Meerwein rearrangement to generate a cyclobutyl carbocation, which undergoes intramolecular nucleophilic capture by amide to forge fluorinated cyclobuta[b]indoline derivatives. A polycyclic multi-fluorinated byproduct was also formed through a Ritter-type reaction in some cases.
Water-Soluble Hypervalent Iodine(III) Having an I-N Bond. A Reagent for the Synthesis of Indoles
Xia, Hai-Dong,Zhang, Yan-Dong,Wang, Yan-Hui,Zhang, Chi
supporting information, p. 4052 - 4056 (2018/07/15)
A readily accessible and bench-stable water-soluble hypervalent iodine(III) reagent (phenyliodonio)sulfamate (PISA) with an I-N bond was synthesized, and its structure was characterized by X-ray crystallography. With PISA, various indoles were synthesized via C-H amination of 2-alkenylanilines involving an aryl migration/intramolecular cyclization cascade with excellent regioselectivity in aqueous CH3CN. Notably, using this new method as the key step, not only two drug molecules, indometacin and zidometacin, but also another bioactive molecule, pravadoline, were synthesized.
NH2-directed C-H alkenylation of 2-vinylanilines with vinylbenziodoxolones
Boelke, Andreas,Caspers, Lucien D.,Nachtsheim, Boris J.
supporting information, p. 5344 - 5347 (2017/11/07)
The first directing-group-mediated C-H alkenylation with alkenyl-λ3-iodanes as electrophilic alkene-transfer reagents has been developed. The application of free aromatic amines as challenging but synthetically valuable directing groups in combination with an IrIII catalyst enabled the synthesis of highly desirable 1, 3- dienes in excellent yields of up to 98% with high to perfect (Z, E) stereoselectivity. A broad substrate scope and further synthetic modifications are demonstrated.
Direct Electrophilic C?H Alkynylation of Unprotected 2-Vinylanilines
Caspers, Lucien D.,Finkbeiner, Peter,Nachtsheim, Boris J.
, p. 2748 - 2752 (2017/03/08)
Unprotected aromatic amines can be used as directing groups in metal-catalyzed C?H alkynylations of alkenes. By using low amounts of an IrIIIcatalyst in combination with alkynylbenziodoxolones as electrophilic alkyne-transfer reagents, highly desirable 1,3-enynes were isolated in excellent yields of up to 98 % with Z stereoselectivity. A broad substrate scope as well as the high synthetic utility of the 1,3-enynes render this new method an efficient approach for the synthesis of five- and six-membered heterocycles. Further derivatizations of the 1,3-enynes to highly substituted quinolines through AuI- and N-bromosuccinimide-mediated exo-dig cyclizations were demonstrated.
An efficient synthesis of iminoquinones by a chemoselective domino ortho-hydroxylation/oxidation/imidation sequence of 2-aminoaryl ketones
Chandrasekar, Selvaraj,Sekar, Govidasamy
supporting information, p. 3053 - 3060 (2016/03/19)
An efficient chemoselective domino oxidative homocoupling of 2-aminoaryl ketones in the presence of 2-iodoxybenzoic acid (IBX) for the synthesis of iminoquinone has been developed. The domino reaction proceeds via three consecutive steps, such as domino ortho-hydroxylation of 2-aminoaryl ketones, oxidation of a phenol derivative to benzoquinone and dimerization through imine formation to yield iminoquinone. Importantly, this reaction allows the recycling of the oxidant IBX by recovering the by-product iodosobenzoic acid (IBA) and oxidizing it back to IBX. A four step domino strategy for the synthesis of iminoquinone through in situ generation of 2-amino benzophenone from (2-amino phenyl)(phenyl)methanol was also developed.
Inhibitors of viral replication, their process of preparation and their therapeutical uses
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Page/Page column 46, (2012/11/06)
The present invention relates to compounds, their use in the treatment or the prevention of viral disorders, including HIV.
INHIBITORS OF VIRAL REPLICATION, THEIR PROCESS OF PREPARATION AND THEIR THERAPEUTICAL USES
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Page/Page column 64, (2012/11/06)
The present invention relates to compounds, their use in the treatment or the prevention of viral disorders, including HIV.
Auto-tandem catalysis: Synthesis of acridines by Pd-catalyzed C=C bond formation and C(sp2)-N cross-coupling
Huang, Zhongxing,Yang, Yang,Xiao, Qing,Zhang, Yan,Wang, Jianbo
supporting information, p. 6586 - 6593 (2013/01/15)
A facile palladium-catalyzed synthesis of acridines has been realized by consecutive C=C double bond formation and C-N cross-coupling. A variety of functionalized acridines can be accessed from easily available o-dihalobenzenes and N-tosylhydrazones in a single operation. This one-pot protocol has a wide scope with respect to both coupling partners, and provides an efficient route to functionalized acridine derivatives, which are generally difficult to synthesize by previously known methods.
