58750-87-1Relevant academic research and scientific papers
Synthesis of (±)-pterocarpin and its thia- and aza-analogues in a modular manner
Huang, Qingyun,Wang, Peng,Tian, Yu,Song, Ni,Ren, Sumei,Tao, Jiaxin,Hang, Kaini,Li, Ming
, p. 1385 - 1390 (2015)
Syntheses of racemic pterocarpin, its thia- and aza-pterocarpin have been achieved in a modular manner using sesamol iodide, diethyl malonate and 3-methoxyphenol, 3-methoxythiophenol and N-tosyl-3-methoxyaniline as building blocks. Copper-mediated Hurtley
Characteristic Hydrogen Bonding Observed in the Crystals of Aromatic Sulfonamides: 1D Chain Assembly of Molecules and Chiral Discrimination on Crystallization
Kikkawa, Shoko,Masu, Hyuma,Katagiri, Kosuke,Okayasu, Misaki,Yamaguchi, Kentaro,Danjo, Hiroshi,Kawahata, Masatoshi,Tominaga, Masahide,Sei, Yoshihisa,Hikawa, Hidemasa,Azumaya, Isao
, p. 2936 - 2946 (2019/05/10)
N-Phenylbenzenesulfonamides exist preferentially in (+)- or (-)-synclinal conformations, which place the aromatic rings at both ends in the same direction with a twist. We have systematically analyzed the crystal structure of secondary aromatic sulfonamides bearing methyl, ethyl, and/or methoxy groups on the benzene rings. Intermolecular hydrogen bonding between the sulfonamide protons and sulfonyl oxygens was observed in 81 out of 85 crystals. The intermolecular hydrogen-bonding patterns could be classified into four types, i.e. Dimeric, Zigzag, Helical, and Straight patterns, with retention of the synclinal conformation of the sulfonamide moiety. We investigated the relationship between the hydrogen-bonding pattern and the proportion of the compounds that show chiral crystallization. On the basis of our classification of the intermolecular hydrogen bonds of aromatic sulfonamides, the crystals with Dimeric and Zigzag patterns, which both have enantiomeric synclinal conformers, intrinsically become achiral, except for kryptoracemates. In contrast, a high proportion of compounds with Helical or Straight patterns in the crystals showed chiral crystallization. Our classification is useful for discussion regarding the chirality of molecular assemblies, on the basis of the conformational chirality of the molecules in the crystal.
Corrigendum to “Transition-metal-free synthesis of aromatic amines via the reaction of benzynes with isocyanates” [Tetrahedron Lett. 59 (2018) 671–674](S0040403918300352)(10.1016/j.tetlet.2018.01.022)
Seo, Jeong Hoon,Ko, Haye Min
supporting information, p. 1213 - 1213 (2019/03/23)
The authors regret that the structure of Scheme 3 is shown incorrectly. The structure of the compound 3e' is shown correctly here.[Figure presented] The penultimate paragraph of the “Results and Discussion” section should read as follows: During the investigation of several substrates, we observed the unexpected product 3e' which had a diphenyl backbone with a tosyl amine in 45% yield (Scheme 3). This structure was confirmed by 1H NMR, 13C NMR, and high-resolution mass spectroscopy. The diphenyl scaffold is useful to develop new ligands, or synthesize materials, pharmaceuticals, and natural products.The Authors also note corrections needed to the data of compound 3j in the Supplementary Data files. This should be re-written as follows: 13C NMR (125 MHz, CDCl3) δ 150.4 (dd, 1C, JC–F = 242.8, 8.2 Hz), 148.3 (dd, 1C, JC–F = 240.6, 7.3 Hz), 144.4, 135.6, 133.0 (dd, 1C JC–F = 8.1, 3.3 Hz), 129.9, 127.3, 118.1 (q, 1C, JC-F = 3.3 Hz), 117.8 (dd, 1C, JC–F = 18.2, 1.3 Hz), 111.8 (d, 1C, JC–F = 20.3 Hz), 21.6.The updated Supplementary Data files have been published online with this Corrigendum. The authors would like to apologise for any inconvenience caused.
Facile Chan-Lam coupling using ferrocene tethered N-heterocyclic carbene-copper complex anchored on graphene
Gajare, Shivanand,Jagadale, Megha,Naikwade, Altafhusen,Bansode, Prakash,Rashinkar, Gajanan
, (2019/04/08)
Ferrocene tethered N-heterocyclic carbene-copper complex anchored on graphene ([GrFemImi]NHC@Cu complex) has been synthesized by covalent grafting of ferrocenyl ionic liquid in the matrix of graphene followed by metallation with copper (I) iodide. The [GrFemImi]NHC@Cu complex has been characterized by fourier transform infrared (FT-IR), fourier transform Raman (FT-Raman), CP-MAS 13C NMR spectroscopy, transmission electron microscopy (TEM), thermogravimetric analysis (TGA), energy dispersive X-ray (EDX) analysis, X-ray photoelectron spectroscopy (XPS), Brunauer–Emmett–Teller (BET) surface area analysis and X-ray diffractometer (XRD) analysis. This novel complex served as a robust heterogeneous catalyst for the synthesis of bioactive N-aryl sulfonamides from variety of aryl boronic acids and sulfonyl azides in ethanol by Chan-Lam coupling. Recyclability experiments were executed successfully for six consecutive runs.
Triple Mode of Alkylation with Ethyl Bromodifluoroacetate: N, or O-Difluoromethylation, N-Ethylation and S-(ethoxycarbonyl)difluoromethylation
Polley, Arghya,Bairy, Gurupada,Das, Pritha,Jana, Ranjan
supporting information, p. 4161 - 4167 (2018/09/21)
In this report, we have explored a triple mode of chemical reactivity of ethyl bromodifluoroacetate. Typically, bromodifluoroacetic acid has been used as a difluorocarbene precursor for difluoromethylation of soft nucleophiles. Here we have disclosed nucleophilicity and base dependent divergent chemical reactivity of ethyl bromodifluoroacetate. It furnishes lithium hydroxide and cesium carbonate promoted difluoromethylation of tosyl-protected aniline and electron-deficient phenols respectively. Interestingly, switching the base from lithium hydroxide to 4-N,N-dimethylamino pyridine (DMAP) tosyl-protected anilines afforded the corresponding N-ethylation product. Whereas, highly nucleophilic thiophenols furnished the corresponding S-carboethoxydifluoromethylation product via a rapid SN2 attack to the bromine atom prior to the ester hydrolysis. This mechanistic divergence was established through several control experiments. It was revealed that difluoromethylation reaction proceeds through a tandem in situ ester hydrolysis/decarboxylative-debrominative difluorocarbene formation and subsequent trapping by the soft nucleophile-NHTs or electron-deficient phenolic ?OH groups. In the presence of DMAP the hydrolysis of the ester is perturbed instead a nucleophilic attack at the ethyl moiety provides the N-ethylation product. Hence, besides the development of a practical base-promoted N-difluoromethylation of amines and electron-deficient phenols, divergent reactivity pattern of inexpensive and user-friendly ethyl bromodifluoroacetate has been explored. (Figure presented.).
Transition-metal-free synthesis of aromatic amines via the reaction of benzynes with isocyanates
Seo, Jeong Hoon,Ko, Haye Min
supporting information, p. 671 - 674 (2018/01/19)
An unexpected reaction between benzynes and isocyanates to generate aromatic amines has been developed under transition-metal-free conditions. The in situ prepared anions formed through cleavage of the N–C bond in isocyanates, reacted with aryne precursor
Palladium-Catalyzed Regioselective Synthesis of 3-Arylindoles from N-Ts-Anilines and Styrenes
Youn, So Won,Ko, Tae Yun,Jang, Young Ho
supporting information, p. 6636 - 6640 (2017/05/29)
A Pd-catalyzed intermolecular oxidative annulation between N-Ts-anilines and styrenes was developed. This method offers a straightforward and robust approach to a wide range of 3-arylindoles using readily available starting materials with good functional-group tolerance and high regioselectivity and efficiency. Further elaboration of the products obtained from this process provided access to highly functionalized and structurally diverse indoles, for example, 3-(indol-3-yl)carbazoles, 1,9-dihydropyrrolo-[2,3-b]carbazoles, and 3′-aryl-3,5′-biindoles.
Discovery, Optimization, and Biological Evaluation of Sulfonamidoacetamides as an Inducer of Axon Regeneration
Ku, Jin-Mo,Park, Kyuhee,Lee, Jung Hun,Cho, Kyong Jin,Nam, Yeon-Ju,Jeong, Dae-Youn,Kim, Yu-Han,Kwon, Soonjung,Park, Ju-Young,Yang, Jungeun,Nam, Tae-Gyu,Yoon, Sung-Hwa,Ahn, Sangmee,Choi, Yongmun
, p. 4676 - 4687 (2016/06/13)
Axon regeneration after injury in the central nervous system is hampered in part because if an age-dependent decline in the intrinsic axon growth potential, and one of the strategies to stimulate axon growth in injured neurons involves pharmacological manipulation of implicated signaling pathways. Here we report phenotypic cell-based screen of chemical libraries and structure-activity-guided optimization that resulted in the identification of compound 7p which promotes neurite outgrowth of cultured primary neurons derived from the hippocampus, cerebral cortex, and retina. In an animal model of optic nerve injury, compound 7p was shown to induce growth of GAP-43 positive axons, indicating that the in vitro neurite outgrowth activity of compound 7p translates into stimulation of axon regeneration in vivo. Further optimization of compound 7p and elucidation of the mechanisms by which it elicits axon regeneration in vivo will provide a rational basis for future efforts to enhance treatment strategies.
A highly efficient heterogeneous copper-catalyzed Chan-Lam coupling reaction of sulfonyl azides with arylboronic acids leading to: N -arylsulfonamides
You, Chongren,Yao, Fang,Yan, Tao,Cai, Mingzhong
, p. 43605 - 43612 (2016/05/24)
A heterogeneous Chan-Lam coupling reaction between sulfonyl azides and arylboronic acids was achieved in MeOH at room temperature in the presence of 10 mol% of an l-proline-functionalized MCM-41-immobilized copper(i) complex [MCM-41-l-proline-CuCl] under air, yielding a variety of N-arylsulfonamides in excellent yields. The new heterogeneous copper complex can be prepared from commercially readily available and inexpensive reagents, and recovered by simple filtration of the reaction solution and recycled at least 8 times without any decreases in activity.
Nickel-catalyzed monoarylation of ammonia
Borzenko, Andrey,Rotta-Loria, Nicolas L.,Macqueen, Preston M.,Lavoie, Christopher M.,McDonald, Robert,Stradiotto, Mark
supporting information, p. 3773 - 3777 (2015/03/18)
Structurally diverse (hetero)aryl chloride, bromide, and tosylate electrophiles were employed in the Ni-catalyzed monoarylation of ammonia, including chemoselective transformations. The employed JosiPhos/[Ni(cod)2] catalyst system enables the use of commercially available stock solutions of ammonia, or the use of ammonia gas in these reactions, thereby demonstrating the versatility and potential scalability of the reported protocol. Proof-of-principle experiments established that air-stable [(JosiPhos)NiCl2] precatalysts can be employed successfully in such transformations. Lighten Up: The substrate scope of the title reaction includes (hetero)aryl chloride, bromide, and tosylate electrophiles. The versatility and potential scalability of the reported method is demonstrated by the use of either commercially available stock solutions of ammonia or ammonia gas.
