32585-06-1Relevant academic research and scientific papers
Synthesis of Isonitrile Derivatives of Diglycerides and Carbohydrates as Intermediates for Multicomponent Ugi Reaction
Cheshkov, D. A.,Khrulev, A. A.,Maslov, M. A.,Morozova, N. G.,Nichugovskiy, A. I.,Perevoshchikova, K. A.
, p. 929 - 938 (2021/08/25)
Abstract: Recently, there has been an increase in interest in multicomponent reactions, mainly due to the possibility of assembling of complex organic molecules in just several steps. Isocyanide is a key reagent for the Ugi multicomponent reaction. Isocyanide exhibits dual properties both electrophilic and nucleophilic. Several ways of formation of isonitrile derivatives are known, but the intramolecular dehydration of formamide is considered to be the main method. In this study, we synthesized isonitrile derivatives of dialkyl glycerol and D-glucose which can serve as new useful blocks for the creation of chemical libraries of lipophilic amines with the carbohydrate residue at their terminal nitrogen atom during the further interaction under the conditions of the multicomponent reactions. Structures of all the synthesized compounds were confirmed by physicochemical analytical methods, and these compounds can be used as blocks for the Ugi multicomponent reaction.
Zinc Hydride Catalyzed Chemoselective Hydroboration of Isocyanates: Amide Bond Formation and C=O Bond Cleavage
Sahoo, Rajata Kumar,Sarkar, Nabin,Nembenna, Sharanappa
supporting information, p. 11991 - 12000 (2021/04/19)
Herein, a remarkable conjugated bis-guanidinate (CBG) supported zinc hydride, [{LZnH}2; L={(ArHN)(ArN)?C=N?C=(NAr)(NHAr); Ar=2,6-Et2-C6H3}] (I) catalyzed partial reduction of heteroallenes via hydroboration is r
Synthesis ofN-alkylated lipopeptides and their application as organocatalysts in asymmetric Michael addition in aqueous environments
Corrêa, Arlene G.,Delgado, José A. C.,Fernandes, Vitor A.,Paix?o, Márcio W.,Vicente, Fidel E. M.,de la Torre, Alexander F.
supporting information, p. 14050 - 14057 (2021/08/16)
A library ofN-alkylated lipopeptide organocatalysts were synthesized through an isocyanide-based multicomponent reaction. Various structural motifs were tunably introduced on the catalyst backbone with the aim of incorporating amphiphilic features. Conseq
A more sustainable and highly practicable synthesis of aliphatic isocyanides
Waibel,Nickisch,M?hl,Seim,Meier
supporting information, p. 933 - 941 (2020/02/21)
Synthesis protocols to convert N-formamides into isocyanides using three different dehydration reagents (i.e. p-toluenesulfonyl chloride (p-TsCl), phosphoryl trichloride (POCl3) and the combination of triphenylphosphane (PPh3) and iodine) were investigated and optimized, while considering the principles of green chemistry. Comparison of the yield and the E-factors of the different synthesis procedures revealed that, in contrast to the typically applied POCl3 or phosgene derivatives, p-TsCl was the reagent of choice for non sterically demanding aliphatic mono- or di-N-formamides (yields up to 98% and lowest E-factor 6.45). Apart from a significantly reduced E-factor, p-TsCl is cheap, offers a simplified reaction protocol and work-up, and is less toxic compared to other dehydration reagents. Thus, this procedure offers easier and greener access to aliphatic isocyanide functionalities.
A double-carbamate aliphatic chain organic silane quaternary ammonium salt compound and its preparation and use
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Paragraph 0033-0036, (2017/03/18)
The invention relates to a propyl dimethicone formic ether aliphatic chain organosilane quaternary ammonium salt compound and preparation as well as application thereof. The structural formula of the compound is shown in the Specification, wherein X is Cl, Br and I; n ranges from 1 to 19, and m ranges from 1 to 9. The preparation method comprises the steps of mixing 3-dimethylamino-1,2-propylene glycol, triethylamine, methylbenzene and prepared aliphatic chain isocyanate, heating to 80 DEG C, and generating reation for 10 hours to obtain a carbamic acid ester midbody; mixing the carbamic acid ester midbody and haloalkylized trimethoxy silane, adding or not adding methylbenzene to heat the materials, cooling to a room temperature, and washing the product to obtain the propyl dimethicone formic ether aliphatic chain organosilane quaternary ammonium salt compound. The application of the propyl dimethicone formic ether aliphatic chain organosilane quaternary ammonium salt compound is that a propyl dimethicone formic ether aliphatic chain organosilane quaternary ammonium salt cation surfactant is added into mother liquor synthesized by a zeolite molecular sieve, then stirred and subjected to hydrothermal crystallization, suction filtration, washing, drying and roasting to obtain a multi-stage orifice zeolite molecular sieve. According to the propyl dimethicone formic ether aliphatic chain organosilane quaternary ammonium salt compound and the preparation as well as the application thereof, the pore volume and the specific surface area of the multi-stage orifice zeolite molecular sieve are obviously enlarged.
Multicomponent synthesis of Ugi-type ceramide analogues and neoglycolipids from lipidic isocyanides
Perez-Labrada, Karell,Brouard, Ignacio,Mendez, Inmaculada,Rivera, Daniel G.
experimental part, p. 4660 - 4670 (2012/07/27)
Unique types of ceramide and glycolipid architectures were obtained by means of Ugi reactions incorporating lipidic isocyanides as surrogates of sphingolipids. The multicomponent nature of this approach allowed for a highly efficient assembly process, whe
Anti-fertilization activity of a spirocyclic sesquiterpene isocyanide isolated from the marine sponge Geodia exigua and related compounds
Ohta, Emi,Uy, Mylene M.,Ohta, Shinji,Yanai, Mihoko,Hirata, Toshifumi,Ikegami, Susumu
, p. 1764 - 1771 (2008/12/23)
(-)-10-epi-Axisonitrile-3, a spirocyclic sesquiterpene isocyanide obtained from the marine sponge Geodia exigua, immobilized sperm of sea urchin and starfish to block fertilization at the minimum effective concentration of 0.4 μg/ml. On the other hand, fertilized eggs developed normally to the gastrula stage in the presence of a 250-times higher concentration of the isocyanide. Analysis by 31P NMR revealed an accumulation of phosphocreatine and a depletion of inorganic phosphate in the isocyanide-treated sperm, suggesting that (-)-10-epi-axisonitrile-3 inhibited the phosphocreatine shuttle participating in the high-energy phosphate metabolism, thereby immobilizing sperm to block fertilization. No analogs of (-)-10-epi-axisonitrile-3 containing different functionalities or isocyanides with different carbon skeleton exhibited such activity.
Reactions of Relevance to the Chemistry of Aminoglycoside Antibiotics. Part 14. A Useful Radical-deamination Reaction
Barton, Derek H. R.,Bringmann, Gerhard,Lamotte, Genevieve,Motherwell, William B.,Motherwell, Robyn S. Hay,Porter, Alexander E. A.
, p. 2657 - 2664 (2007/10/02)
Primary, secondary, and tertiary aliphatic or alicyclic isocyanides are smoothly reduced under radical conditions using tri-n-butylstannane to the corresponding hydrocarbons.The relative ease of reduction is tertiary > secondary > primary.Aromatic isocyanides are not reduced under these conditions.The reduction of isothiocyanates (or isoselenocyanates) by tri-n-butylstannanae also affords hydrocarbons, but here the isocyanides have been shown to be intermediates.The reduction of a compound with isocyanide and xanthate functions in a 1,2-relationship gives a smooth radical fragmentation to furnish an olefin.An efficient synthesis of 2-deoxy-D-glucose starting with glucosamine is described.
