- 1-Cyanoformamidines. Formation during the RuO4-mediated oxidation of secondary amines
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When performed in the presence of cyanide and at pH smaller than 5, the RuO4-mediated oxidation of secondary amines Bn-NH-R (1a-b; R=Me, Et) gave mainly 1-cyanoformamidines Bn-NR-C(=NH)-CN (2a-b) and their hydrolysis products Bn-NR-COCN (3a-b), Bn-NR-CN (4a-b), Bn-NR-CONH2 (5a-b). Carboxamides 5a-b can result also directly from 1a-b. (Chemical Equation Presented).
- Florea, Cristina,Stavarache, Cristina,Petride, Horia
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p. 319 - 325
(2016/10/11)
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- RuO4-mediated oxidation of secondary amines. Part 1. Are hydroxylamines the main intermediates?
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The RuO4-catalyzed oxidation of secondary amines Bn-NH-CH2R (1a and b; R=H, Me) gave mainly amides, but minute amounts of nitrones PhCH=N(O)-CH2R (9a and b) and traces of Bn-N(OH)-CH2R (R=H, 4a) were also detect
- Florea, Cristina A.,Petride, Horia
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p. 475 - 486
(2016/07/20)
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- Racemase activity of B. cepacia lipase leads to dual-function asymmetric dynamic kinetic resolution of α-aminonitriles
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Applaudable promiscuity: Racemase-type activity discovered for B. cepacia lipase with N-substituted α-aminonitriles is proposed to involve a C-C bond-breaking/forming mechanism in the hydrolase site of the enzyme, as supported by experimental data and calculations. This promiscuous activity in combination with the transacylation activity of the enzyme enabled the asymmetric synthesis of N-methyl α-aminonitrile amides in high yield (see scheme). Copyright
- Vongvilai, Pornrapee,Linder, Mats,Sakulsombat, Morakot,Svedendahl Humble, Maria,Berglund, Per,Brinck, Tore,Ramstroem, Olof
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supporting information; experimental part
p. 6592 - 6595
(2011/09/15)
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- Dynamic asymmetric multicomponent resolution: Lipase-mediated amidation of a double dynamic covalent system
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The Strecker reaction is one of the most important multicomponent reactions developed, leading to R-aminonitriles that are versatile substrates for many synthetic applications. In the present study, this reaction type has been applied to a double dynamic covalent resolution protocol, leading to efficient C-C- and C-N-bond generation as well as chiral discrimination. The combination of transimination with iminecyanation enabled the dynamic exchange in more than one direction around a single stereogenic center of restricted structure. This multiple exchange process could generate a vast range of compounds from a low number of starting materials in very short time. The resulting double dynamic covalent systems, created under thermodynamic control, were subsequently coupled in a one-pot process with kinetically controlled lipase-mediated transacylation. This resulted in complete resolution of the dynamic systems, yielding the optimal N-acyl-α-aminonitriles for the enzyme, where the individual chemoenzymatic reactions could produce enantiomerically pure acylated N-substituted α-aminonitriles in good yields.
- Vongvilai, Pornrapee,Ramstroem, Olof
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supporting information; experimental part
p. 14419 - 14425
(2010/02/16)
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- Synthesis, characterization and crystallographic studies of three 2-aryl-3-methyl-4-aryl-1,3-thiazolium-5-thiolates
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Mesoionic 2,4-diphenyl-3-methyl-1,3-thiazolium-5-thiolate, 2-(4′-chlorophenyl)-3-methyl-4-phenyl-1,3-thiazolium-5-thiolate and 2-(4′-chlorophenyl)-3-methyl-4-(4′-isopropyl-phenyl)-1,3- thiazolium-5-thiolate were synthesized via N-methyl-C-aryl-glycines, i
- De Athayde-Filho, Petronio Filgueiras,Miller, Joseph,Simas, Alfredo Mayall,Lira, Bruno Freitas,De Souza Luis, José Alixandre,Zuckerman-Schpector, Júlio
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p. 685 - 690
(2007/10/03)
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- Artemisinin derivatives, method for the preparation thereof and pharmaceutical compositions containing the same
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The invention relates to compound of the general formula (I):R—O—A??(I)wherein:R represents the radical of formula (II): A is as defined in the description,and medicinal products containing the same which are useful in treating or in preventing cancer.
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- Useful Synthesis of α-Aminonitriles by Means of Alumina and Ultrasound
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Combined use of alumina and ultrasound facilitates the synthesis of α-aminonitriles under solid-liquid two phase conditions from carbonyl compounds, salts of amines and potassium cyanide in organic solvents.
- Hanafusa, Terukiyo,Ichihara, Junko,Ashida, Tetsuya
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p. 687 - 690
(2007/10/02)
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- Synthesis and central nervous system properties of 2-[(alkoxycarbonyl)amino]-4(5)-phenyl-2-imidazolines
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A series of 2-[(alkoxycarbonyl)amino]-4(5)-phenyl-2-imidazolines was prepared and evaluated for central nervous system (CNS) effects (antidepressant, anticonvulsant, muscle relaxant, and depressant) in animal models. Some separation of those CNS activities was achieved through substitutions on the phenyl and imidazoline moieties. Halo-substituted phenyl compounds were among the most potent antidepressants in this series, while imidazole N-alkylation produced compounds with increased depressant effects (loss of righting reflex, mouse behavior). Comparison of in vitro and in vivo data for pairs of 2-[(methoxycarbonyl)amino]-4(5)-phenyl-2-imidazolines and their parent, 2-amino-4(5)-phenyl-2-imidazolines, suggests that the title compounds were prodrugs for the 2-amino-4(5)-phenyl-2-imidazolines in inhibition of norepinephrine reuptake.
- Weinhardt,Beard,Dvorak,Marx,Patterson,Roszkowski,Schuler,Unger,Wagner,Wallach
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p. 616 - 627
(2007/10/02)
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- New Synthesis of β-Lactams Based on Nitrone Cycloaddition to Nitroalkenes
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Heating a sample of the major 5-nitro-substituted isoxazolidine isomer obtained from the reaction of a C-phenyl-N-alkylnitrone with trans-1-cyano-2-nitroethylene in methanol resulted in ring contraction and formation of 4-phenyl-3-cyano-N-alkyl-2-azetidin
- Padwa, Albert,Koehler, Konrad F.,Rodriguez, Augusto
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p. 282 - 288
(2007/10/02)
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- Studies on Mesoionic Compounds. Part 10. Synthesis and Chemical Properties of Mesoionic 1,2,5-Thiadiazolium-3-olates
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The preparation of a novel mesoionic heterocycle is described; derivatives of 4-aryl-5-alkyl-1,2,5-thiadiazolium-3-olates (6a-f) are obtained by treatment of α-N-substituted aminophenylacetamides with sulphur monochloride followed by base.
- Masuda, Katsutada,Adachi, Jun,Nomura, Keiichi
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p. 1033 - 1036
(2007/10/02)
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- PHOTOREAKTIONEN DES 3-METHYL-4-PHENYLSYDNONS
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A procedure for the synthesis of 3-methyl-4-phenylsydnone (1) is given.UV. irradiation of 1 in solution generates the nitrile-imine 4 which reacts with activated C,C double bonds and with heterocumulenes to give five-membered heterocycles.In contrast to the 2H-azirines which photochemically react with the C,O double bond of phenylisocyanate, 4 adds to the C,N double bond of the latter.
- Pfoertner, Karl-Heinz,Foricher, Joseph
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p. 653 - 657
(2007/10/02)
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