15258-47-6Relevant articles and documents
HETEROCYCLIC COMPOUND
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Paragraph 1770-1771, (2021/04/02)
The present invention provides a compound having a glucosylceramide lowering action (e.g., promoting glucosylceramide metabolism, inhibition of glucosylceramide synthesis, promoting glucosylceramide catabolism, etc.), which is expected to be useful as an
Synthesis of Benzofuran and Indole Derivatives Catalyzed by Palladium on Carbon
Savvidou, Anatoli,IoannisTzaras, Dimitrios,Koutoulogenis, Giorgos S.,Theodorou, Alexis,Kokotos, Christoforos G.
supporting information, p. 3890 - 3897 (2019/06/27)
Benzofurans and indoles are key moieties in many natural products and pharmaceuticals. Herein, we describe a cheap and easy-to-execute strategy for the synthesis of benzofurans and indoles, employing Pd/C as the promoter. A variety of substituted allyl-anilines and allyl-phenols were converted into the desired products in good to excellent yields. Recycling of Pd/C was possible up to five cycles, keeping similar levels of reactivity.
Direct Aryl C?H Amination with Primary Amines Using Organic Photoredox Catalysis
Margrey, Kaila A.,Levens, Alison,Nicewicz, David A.
supporting information, p. 15644 - 15648 (2017/11/20)
The direct catalytic C?H amination of arenes is a powerful synthetic strategy with useful applications in pharmaceuticals, agrochemicals, and materials chemistry. Despite the advances in catalytic C?H functionalization, the use of aliphatic amine coupling partners is limited. Described herein is the construction of C?N bonds, using primary amines, by direct C?H functionalization with an acridinium photoredox catalyst under an aerobic atmosphere. A wide variety of primary amines, including amino acids and more complex amines are competent coupling partners. Various electron-rich aromatics and heteroaromatics are useful scaffolds in this reaction, as are complex, biologically active arenes. We also describe the ability to functionalize arenes that are not oxidized by an acridinium catalyst, such as benzene and toluene, thus supporting a reactive amine cation radical intermediate.
Pentacoordinated Carboxylate π-Allyl Nickel Complexes as Key Intermediates for the Ni-Catalyzed Direct Amination of Allylic Alcohols
Kita, Yusuke,Sakaguchi, Hironobu,Hoshimoto, Yoichi,Nakauchi, Daisuke,Nakahara, Yasuhito,Carpentier, Jean-Fran?ois,Ogoshi, Sensuke,Mashima, Kazushi
supporting information, p. 14571 - 14578 (2015/10/05)
Direct amination of allylic alcohols with primary and secondary amines catalyzed by a system made of [Ni(1,5-cyclooctadiene)2] and 1,1′-bis(diphenylphosphino)ferrocene was effectively enhanced by adding nBu4NOAc and molecular sieves, affording the corresponding allyl amines in high yield with high monoallylation selectivity for primary amines and high regioselectivity for monosubstituted allylic alcohols. Such remarkable additive effects of nBu4NOAc were elucidated by isolating and characterizing some nickel complexes, manifesting the key role of a charge neutral pentacoordinated η3-allyl acetate complex in the present system, in contrast to usual cationic tetracoordinated complexes earlier reported in allylic substitution reactions.
Thiol activated prodrugs of sulfur dioxide (SO2) as MRSA inhibitors
Pardeshi, Kundansingh A.,Malwal, Satish R.,Banerjee, Ankita,Lahiri, Surobhi,Rangarajan, Radha,Chakrapani, Harinath
, p. 2694 - 2697 (2015/06/08)
Drug resistant infections are becoming common worldwide and new strategies for drug development are necessary. Here, we report the synthesis and evaluation of 2,4-dinitrophenylsulfonamides, which are donors of sulfur dioxide (SO2), a reactive sulfur species, as methicillin-resistant Staphylococcus aureus (MRSA) inhibitors. N-(3-Methoxyphenyl)-2,4-dinitro-N-(prop-2-yn-1-yl)benzenesulfonamide (5e) was found to have excellent in vitro MRSA inhibitory potency. This compound is cell permeable and treatment of MRSA cells with 5e depleted intracellular thiols and enhanced oxidative species both results consistent with a mechanism involving thiol activation to produce SO2.
Copper-catalyzed radical cascade cyclization for the synthesis of phosphorated indolines
Zhang, Hong-Yu,Mao, Liu-Liang,Yang, Bin,Yang, Shang-Dong
supporting information, p. 4101 - 4104 (2015/03/30)
A novel and convenient approach to the synthesis of various phosphorated indolines via a copper-catalyzed radical cascade cyclization reaction has been developed. The reaction employs cheap copper as the catalyst and K2S2O8 as the oxidant under mild conditions. Various alkenes and P-radical precursors are compatible with this transformation. Preliminary mechanistic studies reveal that the addition of the P-radical may initiate the reaction, and then oxidative cyclization may be achieved to afford the desired product. This journal is
Highly selective N-allylation of anilines under microwave irradiation
Liu, Meiyu,Wang, Xie,Sun, Xiaoliang,He, Wei
, p. 2711 - 2714 (2014/05/06)
An easy and rapid procedure for the preparation of a variety of mono- and bis-allylated anilines via the reaction of allyl bromide with a wide range of anilines under microwave irradiation is described. This approach allows use of mild conditions and short reaction times to give high selectivities and excellent yields.
Synthesis of indolines, indoles, and benzopyrrolizidinones from simple aryl azides
Brucelle, Fran?ois,Renaud, Philippe
, p. 3048 - 3051 (2012/08/14)
A simple approach to prepare indolines and benzopyrrolizidinones from ortho-azidoallylbenzenes via a tandem radical addition/cyclization is described. The use of triethylborane to initiate and sustain the process provides the best results. Indolines are easily converted into the corresponding indoles by oxidation with manganese dioxide.
Catalytic enantioselective alkene aminohalogenation/cyclization involving atom transfer
Bovino, Michael T.,Chemler, Sherry R.
supporting information; scheme or table, p. 3923 - 3927 (2012/05/20)
Problem solved: The title reaction was used for the synthesis of chiral 2-bromo, chloro, and iodomethyl indolines and 2-iodomethyl pyrrolidines (see scheme). Stereocenter formation is believed to occur by enantioselective cis aminocupration and C-X bond formation is believed to occur by atom transfer. The ultility of the products as versatile synthetic intermediates was demonstrated, as was a radical cascade cyclization sequence. Copyright
Efficient regio- And stereoselective formation of azocan-2-ones via 8-endo cyclization of α-carbamoyl radicals
Fang, Xinqiang,Liu, Kun,Li, Chaozhong
supporting information; experimental part, p. 2274 - 2283 (2010/05/01)
The iodine-atom-transfer 8-endo cyclization of α-carbamoyl radicals was investigated experimentally and theoretically. With the aid of Mg(CIO 4)2 and a bis(oxazoline) ligand, N- ethoxycarbonylsubstituted N-(pent-4-enyl)-2-iodoalkanamides underwent 8-endo cyclization leading to the formation of only the corresponding 3,5-trans-substituted azocan-2-ones in excellent yields. Similarly, the BF 3·OEt2/H2O-promoted reactions of N-ethoxycarbonyl-N-(2-allylaryl)-2-iodoalkanamides afforded exclusively the benzazocanone products with a 3,5-cis configuration in high yields. The bidentate chelation of substrate radicals not only significantly improved the efficiency of cyclization but also resulted in the change of stereochemistry of azocanone products from 3,8-iransto 3,8-cis. Theoretical calculations at the UB3LYP/6-31G* level revealed that the cyclization of N-carbonyl- substituted α-carbamoyl radicals occurs via the E-conformational transition states without the presence of a Lewis acid. On the other hand, the cyclization proceeds via the Z-conformational transition states when the substrates form the bidentate chelation with a Lewis acid. In both cases, the 8-endo cyclization is always fundamentally preferred over the corresponding 7-exo cyclization. The complexed radicals having the more rigid conformations also allow the better stereochemical control in the iodine-atom-abstraction step. To further understand the reactivity of a-carbamoyl radicals, the competition between the 8-endo and 5-exo cyclization was also studied. The results demonstrated that the 8-endo cyclization is of comparable rate to the corresponding 5-exo cyclization for a-carbamoyl radicals with fixed Z-conformational transition states. As a comparison, the 8-endo mode is fundamentally preferred over the 5-exo mode in the cyclization of NH-amide substrates because the latter requires the Z-conformational transition states, whereas the former proceeds via the more stable E-conformational transition states.
