- Chiral building blocks from biomass: 2,5-diamino-2,5-dideoxy-1,4-3,6- dianhydroiditol
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An efficient route towards the synthesis of 2,5-diamino-2,5-dideoxy-1,4-3, 6-dianhydroiditol 4 has been developed resulting in significant improvements in both isolated yields and purity when compared to literature procedures. As a consequence, resin-grad
- Thiyagarajan, Shanmugam,Gootjes, Linda,Vogelzang, Willem,Wu, Jing,Van Haveren, Jacco,Van Es, Daan S.
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Read Online
- Bio-Based Amides from Renewable Isosorbide by a Direct and Atom-Economic Boric Acid Amidation Methodology
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The functionalization of bio-sourced isohexides has proved challenging over the last number of years, especially in polymer and medicinal chemistry. We report herein the synthesis of bio-based amido-isohexides by the known boric acid catalysed amidation reaction. The coupling reaction was successfully performed with aliphatic and aromatic carboxylic acids. The extension of the scope of the reaction to eight Boc-protected amino acids is also described, the products being obtained in moderate to good yields. A preliminary screening of these new potential organocatalysts was carried out for the aldolization of isatin. We describe herein the formation of the amide bond between amines derived from dianhydrohexitols and carboxylic or amino acids mediated by a catalytic quantity of boric acid.
- Janvier, Marine,Moebs-Sanchez, Sylvie,Popowycz, Florence
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supporting information
p. 2308 - 2318
(2016/05/19)
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- NOVEL AZABENZIMIDAZOLE HEXAHYDROFURO[E,2-B]FURAN DERIVATIVES
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Novel compounds of the structural formula (I) are activators of AMP-protein kinase and may be useful in the treatment, prevention and suppression of diseases mediated by the AMPK activated protein kinase. The compounds of the present invention may be usef
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- Direct amination of bio-alcohols using ammonia
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A slightly adapted catalyst system has been successfully applied in the direct amination of primary and secondary alcohols. Moreover, the applicability to diols has been shown, giving high selectivity towards the primary diamines. It was found that the Ru/P ratio as well as the amount of ammonia used are highly important in this system, especially for higher substrate loadings. The catalyst was employed on a larger batch scale for the conversion of isomannide to the corresponding diamine. Additionally, it was shown that the catalyst is stable for at least six consecutive runs. No significant loss of activity and selectivity was observed.
- Pingen, Dennis,Diebolt, Olivier,Vogt, Dieter
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p. 2905 - 2912
(2013/10/21)
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- METHOD FOR PREPARING DIAMINO-DIANHYDRO-DIDEOXYHEXITOLS, PARTICULARLY PREFERABLY 2,5-DIAMINO-1,4:3,6-DIANHYDRO-2,5-DIDEOXY-D-HEXITOL
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Method for preparing diamino-dianhydro-dideoxyhexitols, particularly 2,5-diamino-1,4:3,6-dianhydro-2,5-dideoxy-D-hexitol. The invention related to a method for preparing diamino-dianhydro-dideoxyhexitols, particularly preferably 2,5-diamino-1,4:3,6-dianhydro-2,5-dideoxy-D-hexitol.
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Paragraph 0024
(2013/05/21)
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- Dianhydrohexitols: New tools for organocatalysis. Application in enantioselective Friedel-Crafts alkylation of indoles with nitroalkenes
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A series of hydrogen bonding organocatalysts was synthesized from dianhydrohexitol and was used for the first time in organocatalysis for Friedel-Crafts alkylation of indoles with nitroalkenes. Moderate yields and enantioselectivities were achieved. ARKAT
- Chen, Ling-Yan,Guillarme, Stephane,Saluzzo, Christine
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p. 227 - 244
(2013/06/27)
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- PROCESS FOR THE DIRECT AMINATION OF ALCOHOLS USING AMMONIA TO FORM PRIMARY AMINES BY MEANS OF A XANTPHOS CATALYST SYSTEM
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The present invention relates to a chemocatalytic liquid-phase process for the direct one-stage amination of alcohols to primary amines by means of ammonia in high yields using a catalyst system containing at least one transition metal compound and a xantphos ligand.
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Paragraph 0059
(2014/01/08)
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- METHOD FOR PRODUCING MULTICYCLICAL RING SYSTEMS CARRYING AMINO GROUPS
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The invention relates to a method for the amination of at least one keto group in a multicyclic ring system comprising at least one keto group into an amino group, using at least one enzyme E having transaminase activity.
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Page/Page column 10-11
(2012/03/08)
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- Renewable rigid diamines: Efficient, stereospecific synthesis of high purity isohexide diamines
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We report an efficient three-step strategy for synthesizing rigid, chiral isohexide diamines derived from 1,4:3,6-dianhydrohexitols. These biobased chiral building blocks are presently the subject of several investigations (in our and several other groups
- Thiyagarajan, Shanmugam,Gootjes, Linda,Vogelzang, Willem,Van Haveren, Jacco,Lutz, Martin,Van Es, Daan S.
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p. 1823 - 1829
(2012/04/04)
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- Improved ruthenium-catalyzed amination of alcohols with ammonia: Synthesis of diamines and amino esters
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Diamination of diols: The first homogeneously catalyzed diaminations of primary and secondary diols with ammonia give the corresponding diamines. Other primary as well as secondary alcohols including hydroxy-substituted esters can also be efficiently converted to primary amines. This atom-efficient and selective amination method proceeds in an ammonia atmosphere without additional hydrogen sources. Copyright
- Imm, Sebastian,Baehn, Sebastian,Zhang, Min,Neubert, Lorenz,Neumann, Helfried,Klasovsky, Florian,Pfeffer, Jan,Haas, Thomas,Beller, Matthias
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supporting information; experimental part
p. 7599 - 7603
(2011/10/01)
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- ISOMANNIDE DERIVATIVES AND THEIR USE AS TASTANTS
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The present invention provides isomannide derivatives having structural formula (I) as shown below and certain subgenera or species thereof, as flavoring agents or tastants, flavor or taste modifiers, and/or flavor/taste enhancers, particularly, savory ("
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Page/Page column 39-40
(2011/02/24)
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- Pseudo-peptides derived from isomannide: Inhibitors of serine proteases
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In this paper, we describe the synthesis of a novel class of pseudo-peptides derived from isomannide and several oxazolones as potential inhibitors of serine proteases as well as preliminary pharmacological assays for hepatitis C. Hepatitis C, dengue and West Nile fever are among the most important flaviviruses that share one important serine protease enzyme. Serine proteases belong to the most studied class of proteolytic enzymes and are a primary target in the drug development field. Several pseudo-peptides were obtained in good yields from the reaction of isomannide and oxazolones, and their anti-HCV potential using the HCV replicon-based assay was shown.
- Barros, Thalita G.,Pinheiro, Sergio,Williamson,Tanuri, Amilcar,Gomes Jr.,Pereira, Helena S.,Brindeiro,Neto, Jose B. A.,Antunes,Muri, Estela M. F.
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experimental part
p. 701 - 709
(2010/08/05)
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- Intramolecular cyclization of C2 symmetric and meso-iodo amino alcohols: A synthetic approach to azasugars
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C2 Symmetric and meso-iodo hydroxy ammonium chlorides generated from 2 and 5 have been cyclized under basic conditions to produce various heterocycles chemoselectively, which comprise tetrahydrofurans 7 and 19, piperidines 13, 15 and 2, and pyrrolidines 17 and 18.
- Kang, Sung Ho,Ryu, Do Hyun
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p. 607 - 610
(2007/10/03)
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- SYNTHESIS OF POLYNITRO-2,6-DIOXABICYCLOOCTANES
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Polynitro ether, 4,4,8,8-tetranitro-2,6-dioxabicyclooctane (1), was synthesized in four steps from 1,4:3,6-dianhydromannitol ditosylate.
- Archibald, T. G.,Baum, K.
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p. 1493 - 1498
(2007/10/02)
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