Synthesis of Enantiomerically Enriched α-Bromonitriles from Amino Acids

Synthesis of Enantiomerically Enriched α-Bromonitriles from Amino Acids

Najeh Tka, Jamil Kraïem & Béchir Ben Hassine
pages 735-743, DOI:10.1080/00397911.2011.608142

http://www.tandfonline.com/doi/abs/10.1080/00397911.2011.608142

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Two methods were investigated for the preparation of six chiral α-bromonitriles with different optic purities. The nitrous deamination of amino acids gives α-bromoacids, which react with chlorosulfonyl isocyanate followed by triethylamine to afford α-bromonitriles with moderate enantiomeric excess. However, the dehydration of corresponding α-bromoamids using thionyl chloride gives α-bromonitriles with good enantiomeric excess up to 94%. The use of phosphoryl chloride instead of thionyl chloride results in more than 30% racemization as determined by high-performance liquid chromatograpic analysis.

J. Iran. Chem. Soc., Vol. 8, No. Suppl., February 2011, pp. S119-S128.

http://www.ics-ir.org/jics/archive/v8/S1/Articles/pdf/JICS-8-S1-Article-13.pdf
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Synthesis of Quinolines Using Nano-Flake ZnO as a New Catalyst under Solvent-Free Conditions

M. Hosseini-Sarvari^, Department of Chemistry, College of Science, Shiraz University, Shiraz, 71454, Iran

     Catalytic activity of nano-flake ZnO for synthesis of quinoline derivatives and their related polyheterocycles under solvent-free conditions has been studied. Nano-flake ZnO has been successfully synthesized by conventional heating of a solution approach using ZnOAc.2H₂O and Urea. This method is simple, cost-effective, and environmentally benign and the catalyst can be reused for several times.

Diversity Oriented Syntheses of Conventional Heterocycles by Smart Multi Component Reactions (MCRs) of the Last Decade

Diversity Oriented Syntheses of Conventional Heterocycles by Smart Multi Component Reactions (MCRs) of the Last Decade,  Heiner Eckert

Molecules 2012, 17(1), 1074-1102; doi:10.3390/molecules17011074

http://www.mdpi.com/1420-3049/17/1/1074   copy paste on browser

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 A collection of smart multicomponent reactions (MCRs) with continuative post condensation cyclizations (PCCs) is presented to construct conventional three- to seven-membered heterocyclic compounds in diversity oriented syntheses (DOS). These will provide a high degree of applying economical and ecological advantages as well as of practicability. Water, ionic liquids, and solvent-less syntheses as well as use of various forms of energy as microwave and ultrasonic irradiation are examined and discussed.

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Progress in Microwave-Aided Chemical Synthesis

Progress in Microwave-Aided Chemical Synthesis

Hani Mutlak A. Hassan ^{A B}, Steve Harakeh ^A, Kaltoom A. Sakkaf ^A and Iuliana Denetiu <sup>A

A</sup> King Fahd Medical Research Centre, King Abdulaziz University, PO Box 80216, Jeddah 21589, Kingdom of Saudi Arabia. ^B Corresponding author. Email: hmahassan@kau.edu.sa

Australian Journal of Chemistry - http://dx.doi.org/10.1071/CH12366
Submitted: 5 August 2012  Accepted: 16 September 2012   Published online: 29 October 2012

 LINK IS
 http://www.publish.csiro.au/paper/CH12366.htm



The continuing use of microwave (µwave) energy in chemical synthesis has been impressive over the past decade, with many reports incorporating µwave-based reactions. Two of the major benefits of using µwave heating are the remarkable decrease in reaction times and often high yield of products in comparison with classical heating, an ideal technology for synthetic chemists. Herein, we highlight some exciting examples of its recent utility in organic, medicinal, and natural product synthetic endeavours.

Enabling integrated biorefineries through high-yield conversion of fractionated pentosans into furfural

Enabling integrated biorefineries through high-yield conversion of fractionated pentosans into furfural

Anurag Mandalika and Troy Runge

Green Chem., 2012, Advance Article
DOI: 10.1039/C2GC35759C, Paper 
 http://pubs.rsc.org/en/content/articlelanding/2012/gc/c2gc35759c



 Batch reactive distillation of biomass hydrolysates was employed to produce furfural in high yield using an entirely aqueous acid-catalyzed process. 

 Dilute aqueous solutions of furfural were produced in high yield from biomass hydrolysates using an acid-catalyzed batch reactive distillation process that separated the vapor phase from the aqueous reactant medium. Hot water hydrolysates from hybrid poplar, miscanthus, switchgrass and corn stover were dehydrated using sulfuric acid. The vapor fraction from the reactor was condensed to produce furfural in excess of 85% of the theoretical yield based on total pentose. Using xylose as the model compound, and temperature and acid concentration as the variables, the process conditions were optimized by the construction of a three-level statistical model. Hot water hydrolysis of biomass provided with a cellulose-rich solid fraction which has potential for conversion into pulp or cellulosic ethanol, while the liquid fraction, rich in hemicellulose sugars, was converted into furfural. Fractionating the biomass allows for exploration of the concept of the integrated biorefinery where the hemicellulose sugars are not underutilized or encountered as potential inhibitors during microbial conversions of the solid stream, but are converted into furfural, a valuable chemical precursor. The availability of the cellulose fraction for further conversion into pulp or ethanol gives the current process a major advantage over the conventional batch process used in industry, where theoretical yields do not exceed 45–50% with the conspicuous absence of a usable cellulose stream.

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Preparation of Pentafluorinated Phenyl-Monohydro[60]fullerenes

 https://www.thieme-connect.de/ejournals/abstract/10.1055/s-0032-1316578
 Wenli Shang et al
 Pentafluorinated phenyl-monohydro[60]fullerenes [C₆₀(Ar_f)₅H] are synthesized in good yields via reaction of the corresponding fluorinated phenyl copper reagent, itself prepared in situ from the fluorinated phenyl Grignard reagent (Ar_fMgBr) and copper(I) bromide-dimethyl sulfide complex, with [60]fullerene (C₆₀) in 1,2-dichlorobenzene under a nitrogen atmosphere.

NO METAL IN C-H BOND FORMATION

ChemCatChem 2011, 3, No. 05, 827-829

Recently, several research groups have reported that the C-H bond arylation of aromatic compounds with haloarenes can be promoted by potassium or sodium tert-butoxide, without the addition of any exogenous transition metal species. 

These serendipitous discoveries are highlighted and summarized.

Shuichi Yanagisawa, Kenichiro Itami
tert-Butoxide-Mediated C-H Bond Arylation of Aromatic Compounds with Haloarenes