- Solvent-dependent conformational switching of the aromatic N-methyl amides depending upon the acceptor properties of solvents
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An aromatic N-methyl amide containing N-(2-pyridyl) and 2,6-pyridinedicarboxamide moieties switches its conformation from cis to trans depending upon the acceptor number of solvents.
- Okamoto, Iwao,Nabeta, Mayumi,Yamamoto, Misaki,Mikami, Maiko,Takeya, Tetsuya,Tamura, Osamu
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- Copper(II) complexes of N,N-diisopropylpicolinamide - Solvatochromic and thermochromic phase change of a monomeric complex to a ferromagnetically coupled dimeric complex
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The synthesis and characterization of mononuclear [Cu(L) 2(Cl)2] (1), dinuclear [{CuCl(L)}2(μ-Cl) 2] (2), and another mononuclear complex [Cu(L)2(ClO 4)2] (3) with a bidentate N,N-diisopropylpicolinamide ligand (abbreviated L) are described. Complexes 1 and 2 were obtained from the same reaction mixture and show thermo- and solvatochromic behavior. Complex 1 shows irreversible thermochromism by changing into 2 upon heating at 160 °C. These two complexes also show solvatochromism in various solvents. The coordination geometry of the metal ions in 1 and 3 is distorted octahedral, whereas 2 has CuII ions in a distorted square-pyramidal geometry. Variable-temperature magnetic susceptibility measurements for the dinuclear copper complex show a ferromagnetic interaction between the CuII ions. The chromotropism has been attributed to a change in geometry from octahedral with terminal chloride ligands to a distorted square-pyramidal coordination with bridging chloride ions. A monomer, [Cu(L)2(Cl) 2] (1, L = N,N-diisopropylpicolinamide), and a ferromagnetically coupled dimer, [Cu(L)(Cl)2]2 (2), are obtained from the same reaction mixture. They show thermo- and solvatochromic behavior owing to the change in coordination geometry from a terminally bonded octahedral copper center to a distorted square-pyramidal copper center with bridging chloride ions. Copyright
- Lumb, Isha,Hundal, Maninder Singh,Corbella, Montserrat,Gomez, Veronica,Hundal, Geeta
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- Stimuli-responsive bile acid-based metallogels forming in aqueous media
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The synthesis and gelation properties of a picolinic acid conjugated bile acid derivative in the presence of metal salts along with the stimuli-responsiveness of the systems are reported. The gels are formed in the presence of Cu2+ ions in the solvent systems composed of 30-50% of organic solvent (MeOH, acetonitrile, or acetone) in water. The gels respond to various stimuli: they can be formed upon sonication or shaking, and their gel-sol transformation can be triggered by a variety of chemical species. NMR, MS, and SEM techniques are exploited in order to gain a deeper insight on the self-assembled systems.
- Noponen, Virpi,Toikkanen, Katri,Kalenius, Elina,Kuosmanen, Riikka,Salo, Hannu,Siev?nen, Elina
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- Dipicolinamide compound and synthetic method thereof
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The invention relates to a compound and a synthetic method thereof and particularly discloses a dipicolinamide compound and a synthetic method thereof. The invention aims to solve the technical problems that the pH of the existing Fenton reaction is sligh
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Paragraph 0035; 0037
(2019/12/02)
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- Cobalt-catalyzed, aminoquinoline-directed C(sp2)-H bond alkenylation by alkynes
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A method for cobalt-catalyzed, aminoquinoline- and picolinamide-directed C(sp2)-H bond alkenylation by alkynes was developed. The method shows excellent functional-group tolerance and both internal and terminal alkynes are competent substrates for the coupling. The reaction employs a Co(OAc)2·4 H2O catalyst, Mn(OAc)2 co-catalyst, and oxygen (from air) as a terminal oxidant.
- Grigorjeva, Liene,Daugulis, Olafs
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supporting information
p. 10209 - 10212
(2015/03/31)
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- An unprecedented ring transformation of a 4-(aminomethyl)oxazoline derivative to a 4-(hydroxymethyl)imidazoline
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An optically active 4-(azidomethyl)-2-(2-pyridyl)oxazoline was prepared starting from l-serine and picolinic acid. Reduction of the azide moiety gave the corresponding 4-(aminomethyl)-2-(2-pyridyl)oxazoline, which is not a stable compound but readily unde
- Schulz, Marvin,Christoffers, Jens
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- Directed amination of non-acidic arene C-H bonds by a copper-silver catalytic system
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Amine meets arene: A method for direct amination of β-C(sp 2)-H bonds of benzoic acid derivatives and γ-C(sp 2)-H bonds of benzylamine derivatives has been developed. The reaction is catalyzed by Cu(OAc)2 and a Ag2/s
- Tran, Ly Dieu,Roane, James,Daugulis, Olafs
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supporting information
p. 6043 - 6046
(2013/06/27)
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- Copper-catalyzed, directing group-assisted fluorination of arene and heteroarene C-H bonds
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We have developed a method for direct, copper-catalyzed, auxiliary-assisted fluorination of β-sp2 C-H bonds of benzoic acid derivatives and γ-sp2 C-H bonds of α,α-disubstituted benzylamine derivatives. The reaction employs a CuI cata
- Truong, Thanh,Klimovica, Kristine,Daugulis, Olafs
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supporting information
p. 9342 - 9345
(2013/07/26)
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- Use of tridentate TsDPEN/pyridine ligands in ruthenium-catalysed asymmetric reduction of ketones
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A series of enantiomerically pure tridentate ligands based on the 1,2-diphenylethane-1,2-diamine structure, containing additional pyridine groups, was prepared and tested in asymmetric transfer hydrogenation of ketones using Ru3(CO)12 as a metal source. Alcohols were formed in up to 93% ee in the best cases, and good results were obtained with ortho-haloarylketones.
- Darwish, Moftah O.,Wallace, Alistair,Clarkson, Guy J.,Wills, Martin
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supporting information
p. 4250 - 4253
(2013/07/26)
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- Scope and limitations of auxiliary-assisted, palladium-catalyzed arylation and alkylation of sp2 and sp3 C-H bonds
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The scope of palladium-catalyzed, auxiliary-assisted direct arylation and alkylation of sp2 and sp3 C-H bonds of amine and carboxylic acid derivatives has been investigated. The method employs a palladium acetate catalyst, substrate, aryl, alkyl, benzyl, or allyl halide, and inorganic base in tert-amyl alcohol or water solvent at 100-140 C. Aryl and alkyl iodides as well as benzyl and allyl bromides are competent reagents in this transformation. The picolinic acid auxiliary is used for amine γ-functionalization, and the 8-aminoquinoline auxiliary is used for carboxylic acid β-functionalization. Some optimization of base, additives, and solvent is required for achieving best results.
- Nadres, Enrico T.,Santos, Gerson Ivan Franco,Shabashov, Dmitry,Daugulis, Olafs
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p. 9689 - 9714
(2013/10/22)
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- Iron-catalyzed oxidative C - H/C - H cross-coupling: An efficient route to α-quaternary α-amino acid derivatives
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Fully loaded: A coordinating activation strategy has been developed to furnish α-quaternary α-amino acids through the iron(III)-catalyzed oxidative functionalization of α-C(sp3) - H bonds of α-tertiary α-amino acid esters. The reaction exhibits a broad substrate scope for both α-amino acids and nucleophiles (Nu) as well as good functional-group tolerance (see scheme, DTBP=di-tert-butyl peroxide, DCE=1,2-dichloroethane). Copyright
- Li, Kaizhi,Tan, Guangying,Huang, Jingsheng,Song, Feijie,You, Jingsong
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supporting information
p. 12942 - 12945
(2014/01/06)
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- Highly diastereoselective and enantioselective synthesis of α-hydroxy β-amino acid derivatives: Lewis base catalyzed hydrosilylation of α-acetoxy β-enamino esters
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By design: A series of α-acetoxy-β-enamino esters 1 were synthesized and then subjected to catalytic asymmetric hydrosilylation. In the presence of a chiral Lewis base catalyst, the reactions proceeded smoothly to provide a wide range of chiral α-acetoxy β-amino acid derivatives in high yields with good diastereoselectivities and enantioselectivities. Copyright
- Jiang, Yan,Chen, Xing,Zheng, Yongsheng,Xue, Zhouyang,Shu, Chang,Yuan, Weicheng,Zhang, Xiaomei
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supporting information; experimental part
p. 7304 - 7307
(2011/09/16)
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- Acid-induced conformational alteration of cis-preferential aromatic amides bearing N-methyl-N-(2-pyridyl) moiety
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A series of cis-preferential aromatic N-methyl amides was designed and synthesized, and acid-induced conformational alteration of these compounds was investigated by means of NMR measurements in solution and X-ray crystal structure analysis. Compounds with a terminal N-methyl-N-(2-pyridyl) amide unit showed acid-induced conformational change from cis to trans, while those with a terminal N-methyl-2-pyridinecarboxamide unit showed a change of the carbonyl orientation from anti to syn with retention of cis conformation.
- Okamoto, Iwao,Terashima, Masayuki,Masu, Hyuma,Nabeta, Mayumi,Ono, Kaori,Morita, Nobuyoshi,Katagiri, Kosuke,Azumaya, Isao,Tamura, Osamu
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experimental part
p. 8536 - 8543
(2011/11/28)
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- Synthesis of certain unsubstituted, 9-exo-(dialkylaminomethyl)-, and 9- endo-(aralkyl)-tricyclo [5.2.1.02,6 decane-8-ketoxime esters and ethers with local anesthetic and analgesic activities
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The synthesis of series of unsubstituted, 9-exo-(dialkylaminomethyl)-, and 9-endo-(aralkyl)tricyclo [5.2.1.0(2,6)] decane-8-ketoximes esters and ethers 3a-j, 4a-d, 7a-j and 13a-d from the oxime synthons 2, 6a-e, 12a and 12b, respectively, is described. Al
- Aboul-Enein M, Nabil,El-Azzouny, Aida,Abdallah, Nevine A.,Maklad, Yousreya A.,Saleh, Ola A.,Ebeid
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p. 197 - 208
(2007/10/03)
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- Optically active transition metal complexes 110 1 new rhodium(I) complexes with 2-pyridinecarboxamido ligands
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The reaction of [Rh(cod)Cl]2 with the 2-pyridinecarboxamides 1a-e in the presence of base affords the new complexes 2a-e in which the amides act as bidentate ligands coordinating via pyridine-N and the deprotonated amide-N. The structure of 2a was established by X-ray structure analysis: C14H17N2ORh, triclinic, space group P1 (No. 2), a = 10.034(4) A, b = 10.146(6) A, c = 13.165(4) A, α = 108.09(3)°, β = 91.93(3)°, γ = 89.90(4)°, Z = 2 X 2, R = 0.039, Rw = 0.036.
- Brunner, Henri,Nuber, Bernhard,Prommesberger, Markus
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p. 179 - 185
(2007/10/03)
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- A NOVEL SYNTHESIS OF PYRIDINECARBOXYLIC ACID PIPERAZIDES
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N-Substituted piperazides of pyridinecarboxylic acids were synthesized in the following way: the pyridinecarboxylic acids were converted into (alkoxy-formic acid-pyridinecarboxylic acid) mixed anhydrides by means of alkyl chloroformates, and these were th
- Budai, Z.,Mezei, T.,Lay, A.
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p. 241 - 246
(2007/10/02)
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