Ueber die Acetylglykolsäure

Anschütz, Richard; Bertram, W.

doi:10.1002/cber.19030360194

Cited by 24 publications

(16 citation statements)

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“…Starting materials. 4-Hydroxy-2-oxo-2H-chromene-3-carbonitrile was prepared following the method of Anschutz [2]. 4-Chloro-2-oxo-2H-chromene-3-carbonitrile (1), a starting compound, was prepared from 4-hydroxy-2-oxo-2H-chromene-3-carbonitrile according to the method of Chechi et al [3], modified by Kaljaj et al [4] in order to obtain higher yields (from 35-40% to 96%) and shorter reaction time (from 7 hours to less then 1 hour).…”

Section: Methodsmentioning

confidence: 99%

Synthesis of new condensed coumarin derivatives

Dekic

Dekić

Vučić³

et al. 2007

Facta Univ Phys Chem Technol

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Reactions of 4-chloro-2-oxo-2H-chromene-3-carbonitrile (1) with 4-methylpyridin- 2-ylamine (2) and 6-methoxy-benzothiazol-2-ylamine (3) in acetonitrile containing a catalytic amount of triethylamine gave the new coumarin derivatives 7-imino-10-methyl-7H- 5-oxa-7a,12-diaza-benzo[a]anthracen-6-one (4) and 7-imino-10-methoxy-7H-5-oxa-12- thia-7a,13-diaza-indeno[1,2-b]phenanthren-6-one (5) in 52 and 39% yields, respectively. The novel compounds were subjected to acid hydrolysis giving the corresponding oxoderivatives 10-methyl-5-oxa-7a,12-diaza-benzo[a]anthracene-6,7-dione (6) and 10- methoxy-5-oxa-12-thia-7a,13-diaza-indeno[1,2-b]phenanthrene-6,7-dione (7) in 64 and 58% yields, respectively. The structural assignments of the synthesized compounds were based on elemental analyses, IR and proton NMR spectra.

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Section: Methodsmentioning

confidence: 99%

Synthesis of new condensed coumarin derivatives

Dekic

Dekić

Vučić³

et al. 2007

Facta Univ Phys Chem Technol

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“…C 50,13 H 7,36 C1 18,51 N 7,31Y0 Gef. ,,49,98 ,,7,40 ,,18,51 ,,7,34% Die 3 Hexan-Phasen (total 75 ml) wurden vereinigt und rnit wenig Natriumsulfat getrocknct (Hexan-Extrakt). Die vereinigtcn Wasser-Phasen (total 75 ml) extrahierte man dreimal mit je 25 ml Methylenchlorid, welches nach Waschen mit 10 ml einer 10-proz.…”

Section: Methyzenchlorid-extrukt (Kurvenunclassified

Über die Synthese von Phosphamidon und seinen Abbau in Pflanzen

Anliker¹,

Beriger²,

Geiger³

et al. 1961

Helvetica Chimica Acta

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“…The products were isolated in good yields and could be used in subsequent transformations without purification. In the following step a solution of 3 and acetylglyoxylic acid 4a [8] was treated with POCl 3 in the presence of triethylamine as the base. The 3-acetoxy-β-lactams 5a -g were produced in good to excellent yields after recrystallization or flash chromatography (Scheme 3).…”

Section: Resultsmentioning

confidence: 99%

An Efficient and Simple Procedure for the Preparation of α-Keto-β-lactams

2000

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585α-Keto-β-lactams 1 are at the crossroads of many important transformations leading to bioactive compounds [1]. Recently, we used yeast-catalyzed reduction of 1-(4-methoxyphenyl)-4-phenyl-2,3-azetidindione as a key step in a biocatalytic approach to the synthesis of the paclitaxel C-13 side chain (Scheme 1) [2]. To investigate other 4-substituted α-keto-β-lactams as substrates for microbial reductions and subsequent conversions to optically pure C-13 side-chain analogs we required a simple, efficient, and general protocol for the synthesis of these compounds.Abstract. The methods for the preparation of α-keto-β-lactams described in the literature are generally specific for a particular target molecule and lack generality. A short route to several of these compounds has been developed and is deods, therefore, are suitable only for the preparation of compounds with acid-resistant substituents. Thus, low reactivity of the quaternary center in the intermediates A, B, or C (the latter accessible via cyclization of a thio-precursor followed by chlorination) towards nucleophilic attack limits the applicability of these otherwise simple and straightforward syntheses.scribed in this communication. The protocol based on an efficient cyclization procedure followed by hydrolysis and oxidation allows preparation of α-keto-β-lactams 5a -g with sensitive substituents.

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Ueber die Acetylglykolsäure

Cited by 24 publications

References 1 publication

Synthesis of new condensed coumarin derivatives

Synthesis of new condensed coumarin derivatives

Über die Synthese von Phosphamidon und seinen Abbau in Pflanzen

An Efficient and Simple Procedure for the Preparation of α-Keto-β-lactams

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