- Trichloronitromethane with acyl chlorides in the presence of tin(II) chloride: Synthesis of trichloronitro ketones
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Trichloronitromethane adds to acid chlorides in the presence of tin(II) chloride to yield dichloronitro ketones via a substitution reaction. Reduction and dechlorination of the dichloronitro ketones give dichloroamino alcohols and nitro ketones, respectiv
- Demir,Tanyeli,Aksoy,Gulbeyaz,Mahasneh
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- Synthetic method of 2,2-dichloro-N-[2-(2-furyl)-2-hydroxyethyl]acetamide and application thereof
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The invention discloses a synthetic method of 2,2-dichloro-N-[2-(2-furyl)-2-hydroxyethyl]acetamide and application thereof. According to the synthetic method, the 2,2-dichloro-N-[2-(2-furyl)-2-hydroxyethyl]acetamide is prepared by carrying out an acylation reaction on alpha-(aminomethyl)-2-furfuryl alcohol serving as a raw material and dichloracetyl chloride under an alkaline condition. The synthetic method provided by the invention is easy to operate, and is simple in process control. The prepared 2,2-dichloro-N-[2-(2-furyl)-2-hydroxyethyl]acetamide is 60 to 80 percent in yield, and can be taken as a standard product for detecting and monitoring the synthesis of furilazole.
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Paragraph 0043; 0045; 0047; 0050
(2019/08/02)
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- One-pot combination of enzyme and Pd nanoparticle catalysis for the synthesis of enantiomerically pure 1,2-amino alcohols
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One-pot combinations of sequential catalytic reactions can offer practical and ecological advantages over classical multi-step synthesis schemes. In this context, the integration of enzymatic and chemo-catalytic transformations holds particular potential for efficient and selective reaction sequences that would not be possible using either method alone. Here, we report the one-pot combination of alcohol dehydrogenase-catalysed asymmetric reduction of 2-azido ketones and Pd nanoparticle-catalysed hydrogenation of the resulting azido alcohols, which gives access to both enantiomers of aromatic 1,2-amino alcohols in high yields and excellent optical purity (ee >99%). Furthermore, we demonstrate the incorporation of an upstream azidolysis and a downstream acylation step into the one-pot system, thus establishing a highly integrated synthesis of the antiviral natural product (S)-tembamide in 73% yield (ee >99%) over 4 steps. Avoiding the purification and isolation of intermediates in this synthetic sequence leads to an unprecedentedly low ecological footprint, as quantified by the E-factor and solvent demand.
- Schrittwieser, Joerg H.,Coccia, Francesca,Kara, Selin,Grischek, Barbara,Kroutil, Wolfgang,D'Alessandro, Nicola,Hollmann, Frank
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p. 3318 - 3331
(2013/12/04)
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- De novo asymmetric approaches to 2-amino-n-(Benzyloxycarbonyl)-1-(2'fury)ethanol and 2-amino-n-(tert-butoxycarbonyl)-1-(2'furyl)ethanol
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Several methods were investigated for the de novo asymmetric synthesis of 2-amino-N-(benzyloxycarbonyl)-1-(2'-furyl)ethanol and 2-amino-N-(tert-butoxycarbonyl)-1-(2'-furyl)ethanol. A five step procedure was developed for the practical preparation of optically pure 2-amino-N-benzyloxycarbonyl)-1-(2'-furyl)ethanol and a shorter 2-step procedure was developed for 2-amino-N-(tert-butoxycarbonyl)-1-(2'-furyl)ethanol. Both routes used a Noyori reduction to install the asymmetry.
- Haukaas, Michael H.,Li, Miaosheng,Starosotnikov, Alexey M.,O'Doherty, George A.
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experimental part
p. 1549 - 1559
(2009/09/06)
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- Enantioselective synthesis of N-Cbz-protected 6-amino-6-deoxymannose, -talose, and -gulose
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equation presented The enantioselective synthesis of three 6-amino-6-deoxy sugars has been achieved in six to eight steps from furfural. A sequence of diastereoselective oxidation and reduction reactions produced Cbz-protected 6-aminomannose from furfuryl alcohol 3. The incorporation of a Mitsunobu reaction into the reaction sequence allows for the selective synthesis of both N-Cbz-protected 6-aminotalose and 6-aminogulose. The overall procedure allows for the synthesis of either enantiomer of these three aminosugars.
- Haukaas, Michael H.,O'Doherty, George A.
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p. 3899 - 3902
(2007/10/03)
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- Process for the preparation of 2-(2-furyl)ethanol amine
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The invention disclosed herein relates to a process for producing heterocyclic ethanolamines, especially 2-(2-furyl)ethanolamine.
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- Synthetic Versatility of N(Silylmethyl)imines: Water-Induced Generation of N-Protonated Azomethine Ylides of Nonstabilized Type and Fluoride-Induced Generation of 2-Azallyl Anions
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N-(Silylmethyl)imines generate N-protonated azomethine ylides of nonstabilized type when treated with water in HMPA, which undergo stereospecific and regioselective cycloadditions with electron-poor olefins affording N-unsubstituted pyrrolidines.On the other hand, fluoride-induced desilylation of the imines leads to 2-azallyl anions which are found to be synthetic equivalents of aminomethyl anion in the Michael additions with electron-poor olefins and nucleophilic additions with carbonyl compounds.
- Tsuge, Otohiko,Kanemasa, Shuji,Hatada, Akira,Matsuda, Koyo
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p. 2537 - 2546
(2007/10/02)
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