- Indirect monoalkylation of primary and secondary amines by reductive decyanation of α-aminonitriles with sodium cyanoborohydride-mercury bis(trifluoroacetate)
-
Secondary and tertiary amines are prepared from α-aminonitriles by selective reductive cleavage of the cyanide moiety. The α-aminonitriles in this case, function as 'masked' imine or iminium ions and are 'unmasked' by mercury(II) in the presence of sodium cyanoborohydride to obtain the reduced product. Secondary amines may be prepared indirectly from primary amines in good yield without danger of over alkylation.
- Sassaman, Mark B.
-
-
Read Online
- LIPID NANOPARTICLE COMPOSITION
-
Provided herein are lipids that can be used in combination with other lipid components, such as neutral lipids, cholesterol and polymer conjugated lipids, to form lipid nanoparticles for delivery of therapeutic agents (e.g., nucleic acid molecules) for therapeutic or prophylactic purposes, including vaccination.
- -
-
Paragraph 00378
(2021/10/15)
-
- Discovery of benzimidazole analogs as a novel interleukin-5 inhibitors
-
A series of novel hydroxyethylaminomethylbenzimidazole analogs 5a-y were synthesized and evaluated for their IL-5 inhibitory activity using pro-B Y16 cell line. Among them, 2-(((4-(cyclohexylmethoxy)-1H-benzo[d]imidazol-2-yl)methyl)amino)butan-1-ol (5e, 94.3% inhibition at 30 μM, IC50 = 3.5 μM, cLogP = 4.132) and 3-cyclohexyl-2-(((4-(cyclohexylmethoxy)-1H-benzo[d]imidazol-2-yl)methyl)amino) propan-1-ol (5k, 94.7% inhibition at 30 μM, IC50 = 5.0 μM, cLogP = 6.253) showed the most potent inhibitory activity. The essential feature of SAR (Fig. 5) indicated that the chromenone ring can be replaced by a benzimidazole ring to maintain the inhibitory activity. In addition, the hydroxyethylaminomethyl group was suitable for the IL-5 inhibitory activity. Moreover, the hydrophobic substituents on carbon play an important role in the IL-5 inhibitory activity of these analogs. However, N-substituted analogs did not improve inhibitory activity. In addition, MTT assay of 5e and 5k with normal B lymphoblasts revealed that they had no significant effects on cell viability.
- Boggu, Pulla Reddy,Kim, Youngsoo,Jung, Sang-Hun
-
-
- N-Alkylation of Alkylolamines with Alcohols Over Mesoporous Solid Acid–Base Cs–B–Zr Catalyst
-
Abstract: The mesoporous solid acid–base Cs–B–Zr mixed oxides were synthesized using the co-precipitation method followed by a subsequent thermal treatment. The catalytic activity of solid Cs–B–Zr mixed oxide was tested for solvent free acid–base catalysed direct alkylolamines with alcohols as green alkylating agent. The effects of Cs/B/Zr ratio, calcination temperature, reaction conditions, and reaction substrate on the catalytic performance of the catalysts were investigated. The XRD, N2 adsorption–desorption, ICP-OES, FT-IR and NH3/CO2-TPD results showed that the mesoporous structure and acid–base properties of the catalysts play important roles in the reaction. A suitable number of acid and basic sites on the catalyst lead to a high activity for the N-alkylation reaction. Graphical Abstract: A direct N-alkylation of amino alcohol with alcohols has been developed using mixed oxide Cs–B–Zr as an acid–base bifunctionalized catalyst.[Figure not available: see fulltext.]
- Chen, Aimin,Wang, Houyong,Liu, Rui,Bo, Yingying,Hu, Jun
-
p. 1182 - 1193
(2016/07/06)
-
- Synthesis of pyrrole N-derivatives from oxazolidines
-
Transformations of oxazolidine derivatives synthesized from industrially produced amino alcohols, aldehydes, and ketones under basic or acidic catalysis lead to the formation of N-alkyl- and N-(hydroxyalkyl)-substituted pyrroles in 19-81% yields.
- Sadykov, E. Kh.,Stankevich,Lobanova,Klimenko
-
p. 219 - 224
(2014/04/17)
-
- Efficient preparation of secondary aminoalcohols through a Ti(IV) reductive amination procedure. Application to the synthesis and antibacterial evaluation of new 3β-N-[hydroxyalkyl]aminosteroid derivatives
-
An efficient method for the synthesis of various secondary aminoalcohols through a titanium(IV) isopropoxide-mediated reductive amination reaction of ketones is reported. Thus, different ketones gave the expected products in moderate to excellent yields up to 89% in numerous cases. A series of 3β-N-[hydroxyalkyl]aminosteroid derivatives were prepared according to this methodology and evaluated for their in vitro antimicrobial properties against human pathogens. All the compounds showed moderate to excellent activities against Gram-positive bacteria exhibiting similar results against Staphylococcus aureus and Streptococcus faecalis with Minimum Inhibitory Concentrations (MICs) varying from 3.12 to 25 μg/mL. No significant antibacterial activities are encountered against Gram-negative bacteria.
- Salmi, Chanaz,Loncle, Céline,Letourneux, Yves,Brunel, Jean Michel
-
p. 4453 - 4459
(2008/09/20)
-
- Synthesis of β-amino alcohols from aromatic amines and alkylene carbonates using Na-Y zeolite catalyst
-
A simple, efficient, and environmentally benign methodology for the synthesis of β-amino alcohols from aromatic amines and alkylene carbonates in the presence of the highly active and reusable solid base catalyst Na-Y zeolite is demonstrated. Georg Thieme Verlag Stuttgart.
- Shivarkar, Anandkumar B.,Gupte, Sunil P.,Chaudhari, Raghunath V.
-
p. 1374 - 1378
(2007/10/03)
-
- Substituted 2-arylimino heterocycles and compositions containing them, for use as progesterone receptor binding agents
-
This invention relates to 2-arylimino heterocycles, including 2-arylimino-1,3-thiazolidines, 2-arylimino-2,3,4,5-tetrahydro-1,3-thiazines, 2-arylimino-1,3-thiazolidin-4-ones, 2-arylimino-1,3-thiazolidin-5-ones, and 2-arylimino-1,3-oxazolidines, and their use in modulating progesterone receptor mediated processes, and pharmaceutical compositions for use in such therapies.
- -
-
Page column 86
(2010/02/05)
-
- Acid-catalyzed decomposition of cyclohexanespiro-2-oxazolidine
-
Heating cyclohexanespiro-2-oxazolidine at 160-200°C in the presence of protic acids results in its decomposition to give N-(2-hydroxyethyl)cyclohexylamine, N-(2-hydroxyethyl)-4,5,6,7-tetrahydroindole, and 2-cyclohexylidenecyclohexanone. The possible pathways leading to these compounds are discussed.
- Kukharev
-
p. 1482 - 1483
(2007/10/03)
-
- A New Synthesis of Highly Functional Nitrones through a Nitrosoketene Intermediate and Their Use for the Stereoselective Synthesis of Amino Acids
-
Reaction of 5-isonitroso-2,2-dimethyl-1,3-dioxane-4,6-dione with various ketones under reflux in toluene gives 3-oxazolin-5-one 3-oxides (cyclic nitrones) via a nitrosoketene intermediate generated from the isonitroso derivative.The cyclic nitrones can be used for the stereoselective dipolar cycloaddition to electron-rich olefins under high pressure to produce fused isoxazolidines.These isoxazolidines, in turn, are versatile intermediates for the stereoselective preparation of substituted α-amino acids.
- Katagiri, Nobuya,Sato, Hiroshi,Kurimoto, Ayumu,Okada, Makoto,Yamada, Akemi,Kaneko, Chikara
-
p. 8101 - 8106
(2007/10/02)
-
- Fiber-reactive disazo brown dye having vinylsulfone-type reactive group
-
A compound, or a salt thereof, represented by the following formula, STR1 wherein A is a substituted or unsubstituted phenylene or naphthylene group, B is STR2 in which R3 is a hydrogen atom or a lower alkyl, lower alkoxy, acylamino or ureido group, and R4 is a hydrogen atom or a lower alkyl or lower alkoxy group, R1 and R3 are independently a hydrogen atom or a substituted or unsubstituted lower alkyl group, X is a substituted or unsubstituted amino, lower alkoxy, substituted phenoxy or sulfo group, Y is --SO2 CH=CH2 or --SO2 CH2 CH2 Z, in which Z is a group capable of being split by the action of an alkali, and m is 2 or 3, which is useful for dyeing hydroxyl group- or amide group-containing fiber materials to give dyed products of a brown color having excellent fastness properties with good build-up property.
- -
-
-
- OXAZOLIDINES. 1. BASIC CATALYTIC DISPROPORTIONATION OF CYCLOHEXANOSPIRO-2-OXAZOLIDINES: SYNTHESIS OF N-SUBSTITUTED 4,5,6,7-TETRAHYDROINDOLES
-
It has been shown that the basic catalytic disproportionation of cyclohexanospiro-2-oxazolidines in the presence of potasium hydroxide or sodium methylate leads to N-substituted 4,5,6,7-tetrahydroindoles with a yield of up to 73percent.The influence of the character of substituents at the nitrogen atom of oxazolidine on the course of the reaction has been established.
- Kukharev, B.F.,Stankevich, V.K.,Kukhareva, V.A.
-
p. 437 - 439
(2007/10/02)
-
- Reductive Alkylation of β-Alkanolamines with Carbonyl Compounds and Sodium Borohydride
-
A synthesis of secondary alkylalkanolamines from primary alkanolamines in a rapid process in which overalkylation is virtually suppressed is described.The procedure combines the ease of formation of oxazolidines from alkanolamines with aldehydes or ketones in absolute ethanol and the lability of the newly formed C-O bond toward sodium borohydrode.The entire process is carried out in 15-35 min depending on the carbonyl substrate.
- Saavedra, Joseph E.
-
p. 2271 - 2273
(2007/10/02)
-
- BORANE-TETRAHYDROFURAN AS A USEFUL REAGENT IN THE N-MONOALKYLATION OF AMINES AND AMINOALCOHOLS BY CARBONYL COMPOUNDS.
-
A new procedure for the high-yield N-monoalkylation of primary aromatic and aliphatic amines is described.
- Morales, Hilda R.,Perez-Juarez, Martin,Cuellar, Laura,Mendoza, Lourdes,Fernandez, Hector,Contreras, Rosalinda
-
p. 1213 - 1220
(2007/10/02)
-
- Carbostyril derivatives
-
Novel carbostyril derivative and its salt represented by the general formula (1), STR1 wherein R1 is a hydrogen atom, a lower alkyl group, a lower alkenyl group or a phenyl-lower alkyl group; R2 is a hydrogen atom, a lower alkyl group or a group of the formula STR2 wherein A is a lower alkylene group; R3 is a lower alkyl group, a hydroxy lower alkyl group, a lower alkoxy-lower alkyl group, a lower alkanoyloxy-lower alkyl group or a benzoyloxy-lower alkyl group; and R4 is a C3-10 -cycloalkyl group which may have at least one hydroxyl group as the substituent(s) in the cycloalkyl ring, a C3-10 -cycloalkyl-lower alkyl group, a phenyl group, a phenyl-lower alkyl group which may have at least one lower alkoxy group as the substituent(s) in the phenyl ring, a lower alkyl group which may have at least one hydroxyl group as the substituent(s), a heterocyclic ring residue or a lower alkyl group having one heterocyclic ring residue as the substituent; further, R3, R4 and the adjacent nitrogen atom, as well as with or without another nitrogen atom, may form a group of the formula STR3 (wherein R5 is a phenyl group, a C3-10 -cycloalkyl group or a phenyl-lower alkyl group; and B is a methine group or a nitrogen atom); the carbon-carbon bond between the 3- and 4-positions in the carbostyril skeleton is a single or double bond; the substituted position of the group of the formula STR4 is any one of 5-, 6-, 7- or 8-position in the carbostyril skeleton; when the group of the formula STR5 is substituted at 5-, 6-, 7- or 8-position in the carbostyril skeleton, then R2 is a hydrogen atom or a lower alkyl group; alternatively, when R2 is a group of the formula STR6 then 5-, 6-, 7- and 8-positions in the carbostyril skeleton are hydrogen atoms and are not substituted with groups of the formula STR7 and when R3 is a lower alkyl group, then R4 should be neither of a C3-10 -cycloalkyl group, a C3-10 -cycloalkyl-lower alkyl group nor a lower alkyl group, having effects for preventing and treating thrombosis and embolism.
- -
-
-
- Extremely low viscosity adducts of lactams with alcohols
-
Adducts useful as solvents are prepared from lactams and an aliphatic, cycloaliphatic or araliphatic alcohol or thioalcohol. Solutions of the adducts in the lactam, alcohol or thioalcohol are also disclosed as well as a process for preparing the adducts and solutions thereof.
- -
-
-