- Syntheses and Crystal Structures of Methyl N-Substituted-N′-Cyanocarbamimidothioates Derived from Dimethyl N-Cyanodithioiminocarbonate
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Abstract: Reaction of dimethyl N-cyanodithioiminocarbonate and arylamine or alkylamine compounds in the refluxing ethanol solution afforded the according methyl N-substituted-N′-cyanocarbamimidothioates 1–16 in good yields. Compounds 1–16 were characterized by proton nuclear magnetic resonance (1H NMR) and infrared spectroscopies, of which the structures of compounds 1, 2 and 3 (Elgemeie et al. in Acta Cryst E71:104–111, 2015) were established by X-ray crystallography, showing that weak hydrogen-bonding interactions exist in compounds 1–3. Compound 1 crystallizes in the orthorhombic space group Pbca, with a = 6.997(2), b = 7.395(2), c = 36.112(11) ?, and Z = 8. The unit cell of 2 has a monoclinic P21/c symmetry with the cell parameters a = 5.8717(12), b = 4.6598(9), c = 37.799(9) ?, β = 91.126(6)°, and Z = 4. Compound 3 crystallizes in the orthorhombic space group Pbca, with a = 7.123(3), b = 7.374(3), c = 38.538(16) ?, and Z = 8. Graphic Abstract: A series of methyl N-subsituted-N′-cyanocarbamimidothioate compounds were efficiently synthesized via the reaction of arylamine or alkylamine compounds with dimethyl N-cyanodithioiminocarbonate. The structures of compounds 1–3 were characterized by X-Ray crystallography.[Figure not available: see fulltext.]
- Wang, Jun-Ling,Ma, Sen,Zhang, Pei-Zhi,Jia, Ai-Quan,Zhang, Qian-Feng
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p. 295 - 302
(2019/07/17)
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- Controlling Proton and Electron Transfer Rates to Enhance the Activity of an Oxygen Reduction Electrocatalyst
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An electrochemical approach is developed that allows for the control of both proton and electron transfer rates in the O2 reduction reaction (ORR). A dinuclear Cu ORR catalyst was prepared that can be covalently attached to thiol-based self-assembled monolayers (SAMs) on Au electrodes using azide–alkyne click chemistry. Using this architecture, the electron transfer rate to the catalyst is modulated by changing the length of the SAM, and the proton transfer rate to the catalyst is controlled with an appended lipid membrane modified with proton carriers. By tuning the relative rates of proton and electron transfer, the current density of the lipid-covered catalyst is enhanced without altering its core molecular structure. This electrochemical platform will help identify optimal thermodynamic and kinetic parameters for ORR catalysts and catalysts of other reactions that involve the transfer of both protons and electrons.
- Gautam, Rajendra P.,Lee, Yi Teng,Herman, Gabriel L.,Moreno, Cynthia M.,Tse, Edmund C. M.,Barile, Christopher J.
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p. 13480 - 13483
(2018/09/25)
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- Synthesis of Cyclic Guanidines Bearing N-Arylsulfonyl and N-Cyano Protecting Groups via Pd-Catalyzed Alkene Carboamination Reactions
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Palladium-catalyzed carboamination reactions of N-allylguanidines bearing cleavable N-cyano or N-arylsulfonyl protecting groups are described. The reactions afford cyclic guanidine products in good yield, and transformations of substrates bearing internal alkenes proceed with high diastereoselectivity. Deuterium labeling studies indicate these transformations proceed via anti-aminopalladation pathways.
- Peterson, Luke J.,Luo, Jingyi,Wolfe, John P.
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supporting information
p. 2817 - 2820
(2017/06/07)
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- Photoresponsive Molecular Switch for Regulating Transmembrane Proton-Transfer Kinetics
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To control proton delivery across biological membranes, we synthesized a photoresponsive molecular switch and incorporated it in a lipid layer. This proton gate was reversibly activated with 390 nm light (Z-isomer) and then deactivated by 360 nm irradiation (E-isomer). In a lipid layer this stimuli responsive proton gate allowed the regulation of proton flux with irradiation to a lipid-buried O2 reduction electrocatalyst. Thus, the catalyst was turned on and off with the E-to-Z interconversion. This light-induced membrane proton delivery system may be useful in developing any functional device that performs proton-coupled electron-transfer reactions.
- Li, Ying,Tse, Edmund C. M.,Barile, Christopher J.,Gewirth, Andrew A.,Zimmerman, Steven C.
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supporting information
p. 14059 - 14062
(2015/11/25)
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- A one-pot, three-component, microwave-promoted synthesis of 2-amino-substituted 7-amino-1,2,4-triazolo[1,5-a][1,3,5]triazines
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A new, efficient, catalyst-free, one-pot, three-component method for the synthesis of 2-amino-substituted 7-amino-1,2,4-triazolo[1,5-a][1,3,5]triazines using 3,5-diamino-1,2,4-triazoles, cyanamide, and triethyl orthoformate is developed. The reaction proceeds smoothly under microwave-assisted heating. Advantages of the method include using easily available reagents, short reaction times, and operational simplicity.
- Kalinina, Svetlana A.,Kalinin, Dmitrii V.,Dolzhenko, Anton V.
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p. 5537 - 5540
(2013/09/23)
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- IMIDAZOLE VARIANTS AS MODULATORS OF GABA RECEPTOR FOR THE TREATMENT OF GI DISORDERS
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Box No. IV Text of the abstract (Continuation of item 5 of the first sheet) The present invention relates to novel compounds having a positive allosteric GàBAB receptor (GDR) modulator effect, methods for the preparation of said compounds and to their use, optionally in combination with a GABAB agonist, for the inhibition of transient lower esophageal sphincter relaxations, for the treatment of gastroesophageal reflux disease, as well as for the treatment of functional gastrointestinal disorders and irritable bowel syndrome (IBS). A compound of the general formula I
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Page/Page column 49
(2008/06/13)
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- Regioselective preparation of N-substituted 3,5-diamino-1,2,4-oxadiazoles
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Regioselective preparation of 3,5-diamino-1,2,4-oxadiazoles which have a substituent on one or the other amino group has been developed. When 1-substituted 3-cyano-2-ethylisourea (2) was allowed to react with hydroxylamine under basic conditions, 5-amino-3-(substituted amino)-1,2,4-oxadiazole (3) was obtained in good yield. On the other hand, 3-amino-5-(substituted amino)-1,2,4-oxadiazoles (4), a regioisomer of 3, could be synthesized by the reaction of N,O-bis(trimethylsilyl)hydroxylamine (9) with 2 or 1-substituted 3-cyano-2-methylisothiourea (1) and subsequent alcoholysis.
- Suyama, Takayuki,Suzuki, Noriyuki,Nishimura, Masami,Saitoh, Yuka,Ohkoshi, Hiroyuki,Yamaguchi, Jun-Ichi
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p. 873 - 876
(2007/10/03)
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- On triazoles XLV [1]. Synthesis of 5,7-diamino-1,2,4-triazolo[1,5-a][1,3,5]triazines
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The reaction of differently substituted 5-amino-1,2,4-triazoles (5) with isothiourea derivatives (3) to yield isomeric 5,7-diamino-1,2,4-triazolo[1,5-a][1,3,5]triazines (6 and 7), previously described as not proceeding in melt, was performed in different solvents as well as in the melt at 150-160°. It was proved that the above reaction had rather general validity. The structure of isomers 6 and 7 were proved spectroscopically. The structure of 6/5 (Q = ethylamino) was corroborated with single crystal X-ray diffraction determination, as well.
- Berecz, Gabor,Pongo, Laszlo,Koevesdi, Istvan,Reiter, Jozsef
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p. 327 - 334
(2007/10/03)
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