86926-56-9Relevant academic research and scientific papers
Productive Syntheses of Privileged Scaffolds Inspired by the Recognition of a Diels–Alder Pattern Common to Three Classes of Natural Products
Badarau, Eduard,Reddy, K. Harsha Vardhan,Loudet, Aurore,Simon, Charles,Trembleau, Laurent,Claerhout, Stijn,Pair, Etienne,Massip, Stéphane,Breton, Philippe,Lesur, Brigitte,Goldstein, Solo,Fourquez, Jean-Marie,Henlin, Jean Michel,Ghosez, Léon
, p. 15477 - 15481 (2020)
Identification of a common Diels–Alder pattern in three classes of bioactive natural products led us to study the synthesis and cycloaddition of a new class of cyclic dienes readily available from β,γ-unsaturated lactams. A practical and readily scalable route to the parent p-methoxybenzyl-protected 6- and 7-membered β,γ-unsaturated lactams was developed. These were readily transformed into the corresponding O-silylated dienes, which were reacted with dimethyl and diethyl fumarate to yield stereoselectively highly functionalized bicyclic adducts. These exhibited unexpected and versatile transformations upon acid hydrolysis depending on the nature of the dienophile substituents and the acid catalyst. All reactions have been performed on multigram quantities. These transformations provide a convenient, economical, and easily scalable pathway for the rapid construction of functionally and stereochemically dense privileged scaffolds for the construction of libraries of natural products-inspired molecules of pharmacological relevance.
Synthesis of C3,C4-Disubstituted Indoles via the Palladium/Norbornene-Catalyzed ortho-Amination/ ipso-Heck Cyclization
Dong, Guangbin,Rago, Alexander J.
, p. 3755 - 3760 (2021/05/29)
Herein, we report the synthesis of C3,C4-disubstituted indoles via the palladium/norbornene cooperative catalysis. Utilizing N-benzoyloxy allylamines as the coupling partner, a cascade process involving ortho-amination and ipso-Heck cyclization takes plac
OXALAMIDO-SUBSTITUTED TRICYCLIC INHIBITORS OF HEPATITIS B VIRUS
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Page/Page column 50; 53-54, (2020/12/07)
The present invention relates to compounds that are inhibitors of hepatitis B virus (HBV). Compounds of this invention are useful alone or in combination with other agents for treating, ameliorating, preventing or curing HBV infection and related conditions. The present invention also relates to pharmaceutical compositions containing said compounds.
Nickel(II) Catalyzed Hydroboration: A Route to Selective Reduction of Aldehydes and N-Allylimines
Hossain, Istiak,Schmidt, Joseph A. R.
, p. 1877 - 1884 (2020/05/25)
A cationic [(iminophosphine)nickel(allyl)]+ complex was found to be sufficiently electrophilic to activate aldehydes and N-allylimines to undergo hydroboration with pinacolborane (HBpin) under mild reaction conditions. The catalyst displayed excellent selectivity toward aldehydes in the presence of ketones. A wide variety of functional groups were tolerated, including halogens, NO2, CN, OMe, and alkenes for both aldehydes and imines. Electron-rich substrates were found to be significantly more reactive than their electron poor counterparts, a feature that was correlated to their enhanced ability to coordinate to the Lewis acidic nickel center.
Carbonylative C?C Bond Activation of Electron-Poor Cyclopropanes: Rhodium-Catalyzed (3+1+2) Cycloadditions of Cyclopropylamides
Dalling, Andrew G.,Yamauchi, Takayuki,McCreanor, Niall G.,Cox, Lydia,Bower, John F.
supporting information, p. 221 - 225 (2018/12/11)
Rh-catalyzed carbonylative C?C bond activation of cyclopropylamides generates configurationally stable rhodacyclopentanones that engage tethered alkenes in (3+1+2) cycloadditions. These studies provide the first examples of multicomponent cycloadditions t
Synthesis of Cyclic N-Hydroxylated Ureas and Oxazolidinone Oximes Enabled by Chemoselective Iodine(III)-Mediated Radical or Cationic Cyclizations of Unsaturated N-Alkoxyureas
Peilleron, Laure,Retailleau, Pascal,Cariou, Kevin
, p. 5160 - 5169 (2019/11/11)
In this study we describe the reactivity of unsaturated N-alkoxyureas in the presence of different combinations of a hypervalent iodine(III) reagent and a bromide source or TEMPO. Three complementary cyclizations can be achieved depending on the reaction conditions. On the one hand, PIFA with pyridinium bromide leads to an oxybromination reaction. On the other hand, bis(tert-butylcarbonyloxy)iodobenzene with tetrabutylammonium bromide or TEMPO triggers aminobromination or aminooxyamination reactions, respectively. Control experiments showed that the three reactions proceed through distinct mechanisms: the first process is ionic while the other two follow a radical manifold. (Figure presented.).
Design, Synthesis, and Biological Evaluation of 1-Benzylamino-2-hydroxyalkyl Derivatives as New Potential Disease-Modifying Multifunctional Anti-Alzheimer's Agents
Panek, Dawid,Wi?ckowska, Anna,Jończyk, Jakub,Godyń, Justyna,Bajda, Marek,Wichur, Tomasz,Pasieka, Anna,Knez, Damijan,Pi?lar, Anja,Korabecny, Jan,Soukup, Ondrej,Sepsova, Vendula,Sabaté, Raimon,Kos, Janko,Gobec, Stanislav,Malawska, Barbara
, p. 1074 - 1094 (2018/05/26)
The multitarget approach is a promising paradigm in drug discovery, potentially leading to new treatment options for complex disorders, such as Alzheimer's disease. Herein, we present the discovery of a unique series of 1-benzylamino-2-hydroxyalkyl deriva
Photoinduced radical-initiated carboxylative cyclization of allyl amines with carbon dioxide
Wang, Mei-Yan,Cao, Yu,Liu, Xi,Wang, Ning,He, Liang-Nian,Li, Si-Han
supporting information, p. 1240 - 1244 (2017/08/18)
Visible light-promoted CO2 upgrading: a highly efficient and metal-free photochemical method for the carboxylative cyclization of allyl amines with CO2 is reported to prepare perfluoroalkylated oxazolidinones with high efficiency under ambient conditions by using perfluoroalkyl iodides as radical sources.
Visible light-induced intramolecular dearomative cyclization of α-bromo-N-benzyl-alkylamides: Efficient construction of 2-azaspiro[4.5]decanes
Hu, Bei,Li, Yuyuan,Dong, Wuheng,Ren, Kai,Xie, Xiaomin,Wan, Jun,Zhang, Zhaoguo
supporting information, p. 3709 - 3712 (2016/03/05)
An efficient intramolecular dearomative cyclization via visible light-induced photoredox catalysis allows for a highly regioselective dearomative cyclization of α-bromo-N-benzyl-alkylamides to construct 2-azaspiro[4.5]decanes in the presence of an iridium catalyst.
Rhodium-Catalyzed Regiodivergent Hydrothiolation of Allyl Amines and Imines
Kennemur, Jennifer L.,Kortman, Gregory D.,Hull, Kami L.
supporting information, p. 11914 - 11919 (2016/10/06)
The regiodivergent Rh-catalyzed hydrothiolation of allyl amines and imines is presented. Bidentate phosphine ligands with larger natural bite angles (βn ≥ 99°), for example, DPEphos, dpph, or L1, promote a Markovnikov-selective hydrothiolation in up to 88% yield and >20:1 regioselectivity. Conversely, when smaller bite angle ligands (βn ≤ 86°), for example, dppbz or dppp, are employed, the anti-Markovnikov product is formed in up to 74% yield and >20:1 regioselectivity. Initial mechanistic investigations are performed and are consistent with an oxidative addition/olefin insertion/reductive elimination mechanism for each regioisomeric pathway. We hypothesize that the change in regioselectivity is an effect of diverging coordination spheres to favor either Rh-S or Rh-H insertion to form the branched or linear isomer, respectively.
