- Method for synthesizing 3 - phthalatic imide - 2 - oxo-butyl - 1, 2 - double-thiosemicarbazone method
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The invention relates to a novel method of synthesizing 3-phthalimide-2-oxobutryaldehyde-1, 2-bis-thiosemicarbazide. The novel method comprises the following steps: synthesizing 3-nitro-2-butanol with acetaldehyde and nitroethane as starting raw materials, then carrying out reduction on 3-nitro-2-butanol to generate 3-amino-2-butanol, carrying out reaction on 3-amino-2-butanol and phthalic anhydride to generate N-(1-methyl-2-hydroxypropyl) phthalimide, respectively carrying out oxidation by two steps to form 3-phthalimide-2-oxo-butyraldehyde, and finally carrying out condensation on 3-phthalimide-2-oxo-butyraldehyde and thiosemicarbazide to obtain a target product. The 3-phthalimide-2-oxobutryaldehyde-1, 2-bis-thiosemicarbazide has obvious inhibition action on replication of herpes simplex I type (HSV-I) and II I type (HSV-II) viruses in tissue culture cells; at present, the 3-phthalimide-2-oxobutryaldehyde-1, 2-bis-thiosemicarbazide is mainly clinically used for treating skin diseases caused by herpesvirus and sexually transmitted diseases caused by human papillomavirus (HSV) and has good curative effect.
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Paragraph 0051; 0052; 0053; 0054; 0055; 0074; 0075; 0076
(2017/04/12)
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- Solvent-Free Henry and Michael Reactions with Nitroalkanes Promoted by Potassium Carbonate as a Versatile Heterogeneous Catalyst
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The use of a simple weak inorganic base such as potassium carbonate facilitated the formation of carbon-carbon bonds through both the Henry and the Michael reactions with nitrocompounds. The application of this catalyst under environmentally friendly solventless heterogeneous conditions gave satisfactory to good yields of β-nitroalcohols, involving aliphatic and aromatic starting materials, as well as high to excellent yields in the formation of Michael adducts using several different Michael acceptors and nitroalkanes.
- Bosica, Giovanna,Polidano, Kurt
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- Nanoporous lanthanide metal-organic frameworks as efficient heterogeneous catalysts for the Henry reaction
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A series of self-assembled lanthanide coordination polymers formulated as [La(L1)2]n·1n(DMF)H·3n(DMF) (1), [Ce(L1)2]n·1n(DMF)H·2n(DMF) (2), [Sm(L1)2]n·1n(HCONH2)H·2n(HCONH2) (3), [La(L2)(HL2)(H2O)(DMF)2]n (4) and [Ce(L2)(HL2)(H2O)(DMF)2]n (5) [H2L1: 2-acetamidoterephthalic acid and H2L2: 2-benzamidoterephthalic acid] has been synthesized from the reactions of H2L1 or H2L2 with different lanthanide salts under hydrothermal conditions and characterized by elemental analysis, IR spectroscopy, X-ray single-crystal diffraction, powder X-ray diffraction, thermogravimetry and photoluminescence spectroscopy. X-ray diffraction analyses reveal that frameworks 1-3 have similar types of three-dimensional structures, composed of L12- ligands and trinuclear lanthanide nodes, in which two crystallographically independent lanthanide atoms are present. Frameworks 4 and 5 are isostructural, featuring a double chain-type one-dimensional coordination polymer which expands to 3D by means of H-bond interactions. These frameworks act as heterogeneous polymeric solid catalysts for the nitroaldol (Henry) reaction of different aldehydes with nitroalkanes, in water, and can be recycled without losing appreciable activity.
- Karmakar, Anirban,Hazra, Susanta,Guedes Da Silva, M. Fátima C.,Paul, Anup,Pombeiro, Armando J. L.
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p. 1337 - 1349
(2016/03/01)
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- Synthesis of 2,2′-bipyrrole-5-carboxaldehydes and their application in the synthesis of B-ring functionalized prodiginines and tambjamines
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Facile, versatile, and cost-effective synthetic routes for the preparation of a range of new 3-alkyl-, 4-alkyl-, 3,4-dialkyl-, and 3-halo-4-alkyl-2, 2′-bipyrrole-5-carboxaldehydes have been developed. These 2,2′-bipyrrole-5-carboxaldehydes offer interesting potential as building blocks for making bioactive natural and unnatural products, as demonstrated by the synthesis of B-ring functionalized prodiginines (PGs) and tambjamines.
- Kancharla, Papireddy,Reynolds, Kevin A.
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p. 8375 - 8385
(2013/09/02)
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- PROCESS FOR THE PREPARATION OF NITROALCOHOLS
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A process of preparing a nitroalcohol, e.g., 2-nitro-2-methyl-1-propane, from a nitropolyol, e.g., 2-nitro-2 -methyl-1,3-propanediol, the process comprising the step of contacting under hydrogenation conditions the nitropolyol with hydrogen, a hydrogenation catalyst and, optionally, a chelating agent.
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Paragraph 0026
(2013/09/26)
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- Chemo-enzymatic synthesis of a multi-useful chiral building block molecule for the synthesis of medicinal compounds
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Optical resolution of 2-methyl-2-nitrobut-3-en-1-ol has been accomplished using a low-temperature lipase-catalyzed transesterification carried out at -40°C.
- Nakano, Toshiki,Yagi, Yusuke,Miyahara, Mizuki,Kaminura, Akio,Kawatsura, Motoi,Itoh, Toshiyuki
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experimental part
p. 6747 - 6757
(2011/10/18)
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- Nitroaldol-reaction of aldehydes in the presence of non-activated Mg:Al 2:1 hydrotalcite; A possible new mechanism for the formation of 2-aryl-1,3-dinitropropanes
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Commercially available, non-activated 2:1 Mg:Al hydrotalcite catalyzes the nitroaldol reaction between a variety of aromatic and aliphatic aldehydes and simple nitroalkanes such as nitromethane and nitroethane. A new mechanism is proposed for the formation of the 1,3-dinitropropanes. The threo/erythro diastereoselectivity of the nitroethane-adducts was determined by 1H NMR spectroscopy and was found to range from 50:50 to 70:30. The substituents of the aromatic aldehydes influenced the isomer ratio.
- Cwik, Agnieszka,Fuchs, Aliz,Hell, Zoltán,Clacens, Jean-Marc
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p. 4015 - 4021
(2007/10/03)
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- Method of producing organic compounds in presence of oxyethylene ether catalyst and in a solvent minimized environment
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A process of producing organic compounds, such as acetaminophen, nitroalcohols and indoles, employs a catalyst system of an oxyethylene ether and a metal containing inorganic or organic reagent. The oxyethylene ether at least partially complexes the metal of the inorganic or organic reagent. As such, the reactions may be conducted neat. The processes are environmentally friendly and operationally simple.
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- Large scale, efficient synthesis of 9-unsubstituted dipyrrinone
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9-Unsubstituted dipyrrinone 8, the useful precursor for the synthesis of biliverdins, bilirubins, and other bile pigments, was synthesized in large scale and high yield starting from acetaldehyde and nitroethane in eight steps with overall yield 10%. The key intermediate 3,4-dimethyl-2-ethoxycarbonylpyrrole 3 was synthesized via Zard-Barton's method in high yield.
- Chen, Qingqi,Wang, Tianyu,Zhang, Yi,Wang, Qiuan,Ma, Jinshi
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p. 1031 - 1040
(2007/10/03)
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- Diastereoselective access to 3-nitro-4-vinylidenetetrahydrofurans and 3-nitro-4-vinylidenetetrahydropyrans and their conversion into 3,6-dihydro-1,2-oxazines by reverse cope elimination of hydroxylamine precursors
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A new approach to the synthesis of unsaturated nitro-allenyltetrahydrofurans 3 and -tetrahydropyrans 5 has been developed, involving oxa-Michael addition/SN2′ substitution of propargyl and homopropargyl alcohol derivatives 2a and 4h on nitroalkenes1a-g. Complete allylic 1,3-strain control during the cyclization accounts for the observed diastereoselectivity. Reduction of nitro compounds 3 and 5 with SmI2 provided new α-allenylhydroxylamines 7 and 8, which were easily isomerized into 3,6-dihydro-1,2-oxazines 9 and 10 by reverse Cope elimination. Wiley-VCH Verlag GmbH, 2001.
- Dumez, Estelle,Faure, Robert,Dulcere, Jean-Pierre
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p. 2577 - 2588
(2007/10/03)
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- Regioselective synthesis of 5-unsubstituted benzyl pyrrole-2-carboxylates from benzyl isocyanoacetate
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A general synthesis of 5-unsubstituted benzyl pyrrole-2-carboxylates was developed based on the reaction of β-nitroacetates with benzyl isocyanoacetate. The advantage of this route over other pyrrole syntheses was the regiochemical control of the substitution pattern on the pyrrole ring.
- Ono,Katayama,Nisyiyama,Ogawa
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p. 707 - 710
(2007/10/02)
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- Conformation Preferences in Nitro-alcohols: Possible Donor-Acceptor Interactions
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By means of 1H and 13C n.m.r. coupling constants, dilution studies, the effect of solvent, and limited i.r. studies, the configuration and conformation in a group of diastereoisomeric nitro-alcohols, such as 3-nitrobutan-2-ol are assigned.The question of interest concerns the effect of intramolecular hydrogen bonding between nitro and hydroxy on conformation.This effect proved to be weak.The OH n.m.r. signal was split into a doublet, in certain cases; the magnitude of the splitting was not indicative of prevalent hydrogen bonding, in agreement with hydroxy chemical shift, and with vicinal proton coupling constants.The 15N chemical shifts were similar to nitromethane, and not sensitive to the state of isomerism.Deuterium for hydrogen exchange occured at the carbon bearing the nitro group with high retention of configuration.
- Kingsbury, Charles A.,Sopchik, Alan E.,Underwood, Gary,Rajan, Srinavasan
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p. 867 - 874
(2007/10/02)
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