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  • 1
    Electronic Resource
    Electronic Resource
    Regiospecific Allylation of Benzoyl-Substituted Heterocyclic Ketene Aminals and Their Zinc Chloride-Promoted 3-Aza-Cope Rearrangement (1995)
    s.l. : American Chemical Society
    The @journal of organic chemistry 60 (1995), S. 2807-2811 
    Details
    ISSN: 1520-6904
    Source: ACS Legacy Archives
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1021/jo00114a033
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  • 2
    Electronic Resource
    Electronic Resource
    Heterocyclic β-Enamino Esters, 34. New Types of Spiro Compounds by Addition and Cyclization Reactions of 3-(2-Imidazolidinylidene)- and 3-(Tetrahydro-2(1H)-pyrimidinylidene)dihydro-2(3H-furanones with Methyl Acrylate and Dimethyl Acetylenedicarboxylate (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 1926-1934 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Heterocyclische β-Enaminoester, 341). Neue Typen von Spiro-Verbindungen durch Additions- und Ringschlußreaktionen von 3-(2-Imidazolidinyliden)- und 3-(Tetrahydro-2(1H)-pyrimidinyliden)dihydro-2(3H)-furanonen mit Acrylsäure-methylester und Acetylendicarbonsäure-dimethylesterDie 2(3H)-Furanone 1a - e reagieren mit Acrylsäure-methylester in Benzol- oder Dioxanlösung in einer Additions- und Cyclokondensations-Sequenz zu den Spiro-Verbindungen 2a - e. 1a, b ergeben mit Acetylendicarbonsäure-dimethylester die Additionsprodukte 3a, b; hingegen resultieren aus 1c - e in einer verwandten Additions-Cyclokondensationssequenz die Spiro-Verbindungen 4a - c.
    Notes: The 2(3H-furanones 1a - e react with methyl acrylate in benzene or dioxane solution to afford the spiro compounds 2a - e in an addition and cyclocondensation reaction sequence. With dimethyl acetylenedicarboxylate 1a, b give merely the addition products 3a, b, while 1c - e yields the spiro compounds 4a - c in a related addition-cyclocondensation step.
    Additional Material: 5 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19841170521
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  • 3
    Electronic Resource
    Electronic Resource
    Synthesis of ketene aminals with an imidazolidine ring by condensation of 4,5-dihydro-2-(methylithio)-1H-imidazoles with active methylene compounds and some addition and cyclocondensation reactions (1986)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 119 (1986), S. 2208-2219 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthese von Ketenaminalen mit Imidazolidinring durch Kondensation von 4,5-Dihydro-2-(methylthio)-1H-imidazolen mit CH-aciden Methylenverbindungen und einige Additions-und Cyclokondensations-Reaktionen4,5-Dihydro-2-(methylthio)-1H-imidazole 1a, b reagieren mit aktiven Methylenverbindungen 2a-f unter Eliminierung von Methanthiol zu den entsprechend substituierten Methylenimidazolidinen 3a-f und 4c-f. Die Verbindungen 2g-j, die eine aktivere Carbonylgruppe enthalten, ergeben mit 1a unter Eliminierung einer Methylthio- und Acylgruppe 3g-i. 3a, g-i reagieren mit Estern ungesättigter Säuren in einer Additions- und Cyclokondensations-Sequenz zu den entsprechenden Imidazo[1,2-a]pyridinen 5,6 und 7, ergeben aber mit Azodicarbonsäure-diethylester nur die Additionsprodukte 8.
    Notes: The 4,5-dihydro-2-(methylthio)-1H-imidazoles 1a,b react with active methylene compounds 2a-f to afford the corresponding substituted methyleneimidazolidines 3a-f and 4c-f by elimination of methanethiol. The reaction of compounds 2g-j, which contain a more active carbonyl group, with 1a gives 3g-i by elimination of a methylthio group as well as an acyl group, too. 3a,g-i react with esters of α,β-unsaturated acids to afford the corresponding imidazo[1,2-a]pyridines 5,6, and 7 in an addition and cyclocondensation reaction sequence, but with diethyl azodicarboxylate only to give the addition product 8.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19861190715
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  • 4
    Electronic Resource
    Electronic Resource
    Synthesis, Reactions, and Tautomerism of Ketene N,S-Acetals with Benzothiazoline Ring (1990)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 123 (1990), S. 541-547 
    Details
    ISSN: 0009-2940
    Keywords: Ketene N,S-acetals / 1H-Pyrido[2,1-b]benzothiazole, derivatives ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Ketene dithioacetals 2 react with 2-aminothiophenol to afford the corresponding substituted 2(3H)-methylenebenzothiazoles 3. Some compounds 3 react with α,β-unsaturated esters to give 1H-pyrido[2,1-b]benzothiazole derivatives 4 and 5 by an electrophilic addition and cyclocondensation sequence.
    Additional Material: 5 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19901230321
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  • 5
    Electronic Resource
    Electronic Resource
    Synthesis of acetyl-substituted heterocyclic ketene aminals and their deacetylation reaction (1990)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 123 (1990), S. 2141-2145 
    Details
    ISSN: 0009-2940
    Keywords: Ketene aminals, heterocyclic ; Deacetylation ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The acetyl-substituted heterocyclic ketene aminals 3  -  6 were synthesized by the reaction of ketene dithioacetals 2 with diamines. The deacetylation of heterocyclic diacetyl keteneaminals by alkali was studied, and the corresponding monoacetyl derivatives were obtained.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19901231109
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  • 6
    Electronic Resource
    Electronic Resource
    Heterocyclic β-Enamino Esters, 33. Addition and Cyclization Reaction of 3-(2-Imidazolidinylidene)-and 3-(Hexahydro-2-pyrimidinylidene)-2(3H)-furanones with Hydrochloric Acid, Halogens, and Methyl Propiolate (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 1856-1867 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Heterocyclische β-Enaminoester, 33. Additions- und Ringschlußreaktionen der 3-(2-Imidazolidinyliden)- und 3-(Hexahydro-2-pyrimidinyliden)-2(3H)-furanone mit Chlorwasserstoffsäure, Halogenen und Propiolsäure-methylesterDie 3-(2-Imidazolidinyliden)- und 3-(Hexahydro-2-pyrimidinyliden)-2(3H)-furanone 1a - e reagieren unter syn-Addition mit Propiolsäure-methylester in Benzol oder Dioxan zu den Addukten 2a - e. In Alkoholen findet Ringschluß zu den Imidazo[1,2-a]pyridinen und Pyrido-[1,2-a]pyrimidinen 3a - j statt unter Öffnung des γ-Lactonrings. In alkoholischer Lösung entstehen 3a - j direkt. In Abhängigkeit von der Substitution reagieren 1a - e mit Brom oder Chlor zu den halogenierten Hydrohalogeniden 4a - c, 5a - c und 6; sie werden ferner mit Chlorwasserstoffsäure glatt zu den Immoniumsalzen 7a - e protoniert.
    Notes: The 3-(2-imidazolidinylidene)- and 3-(hexahydro-2-pyrimidinylidene)-2(3H)-furanones 1a - e react with methyl propiolate in benzene or dioxane solution to afford the adducts 2a - e via syn- addition. In the presence of alcohols 2a - e are cyclized to give the imidazo[1,2-a]pyridines and pyrido[1,2-a]pyrimidines 3a - j with ring cleavage of the γ-lactone ring; in turn 3a - j are directly formed from 1a - e in alcoholic solution. Upon treatment with bromine or chlorine 1a - e give the halogenated hydrohalides 4a - c, 5a - c, or 6 depending on the individual substituents; they are furthermore smoothly protonated with hydrochloric acid to form the immonium salts 7a - e.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19841170513
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  • 7
    Electronic Resource
    Electronic Resource
    Synthesis of Cycloalkanone-Substituted Ketene Aminals and their Reaction with Ethyl Propiolate (1987)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 120 (1987), S. 1803-1807 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthese von Cycloalkanon-substituierten Keten-aminalen und ihre Reaktion mit Propiolsäure-ethylester2-[Bis(methylthio)methylen]cycloalkanone 1 reagieren mit Diaminen zu 2-[Tetrahydropyrimidin-2(1H)-yliden]cycloalkanonen 2a-e und 2-(2-Imidazolidinyliden)cycloalkanonen 2f, g. Die Ketenaminale 2 ergeben mit Propiolsäure-ethylester in Alkohollösung die 9-[(Alkoxycarbonyl)alkyl]pyrido[1,2-a]pyrimidine 5a-e, 6c, e und 8-[(Alkoxycarbonyl)alkyl]imidazo[1,2-a]pyridine 5f, g, 6g unter Ringöffnung der cyclischen Ketone. Diese leichte Ringöffnung von cyclischen Ketonen ist ungewöhnlich.
    Notes: 2-[Bis(methylthio)methylene]cycloalkanones 1 react with diamines to give the corresponding 2-[tetrahydropyrimidin-2(1H)-ylidene]cycloalkanones 2a-e and 2-(2-imidazolidinylidene)cycloalkanones 2f, g. The ketene aminals 2 react with ethyl propiolate in alcoholic solution to afford 9-[(alkoxycarbonyl)-alkyl]pyrido[1,2-a]pyridines 5a-e, 6c, e, and 8-[(alkoxycarbonyl)alkyl]imidazo[1,2-a]pyridines 5f, g 6g via ring cleavage of the cyclic ketones. This facile ring cleavage of cyclic ketones is unusual.
    Additional Material: 4 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19871201106
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  • 8
    Electronic Resource
    Electronic Resource
    Synthesis of heterocyclic ketene N,O-Acetals and their reactions with α,β-unsaturated esters (1989)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 122 (1989), S. 2011-2016 
    Details
    ISSN: 0009-2940
    Keywords: Ketene N,O-acetals, heterocyclic ; 5H-Oxazolo[2,3-a]pyridine derivatives ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthese von heterocyclischen Keten-N,O acetalen Und ihre Reaktionen mit α,β-ungesättigten EsternKetendithioacetale 2 reagieren mit 2-Aminoethanol oder 1-Amino-2-propanol zu den entsprechenden substitutierten 2-Methylenoxazolidinen 3 und 4. Diese ergeben in einigen Fällen mit α,β-ungesättigten Estern 5H-Oxazolo[3,2-a]pyridin-Derivate über eine Additions- und Cyclokondensations-Sequenz.
    Notes: Ketene dithioacetals 2 react with 2-aminoethanol or 1-amino-2-propanol to afford the corresponding substituted 2-methyleneoxazolidines 3 and 4. In some cases, 3 and 4 react with α,β-unsaturated esters to give 5H-oxazolo[3,2-a]pyridine derivatives 5 by an electrophilic addition and cyclocondensation sequence.
    Additional Material: 4 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19891221029
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  • 9
    Electronic Resource
    Electronic Resource
    Study of Calixarenes, V. Friedel-Crafts Reaction of Calixarenes (1994)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 127 (1994), S. 519-523 
    Details
    ISSN: 0009-2940
    Keywords: Calixarenes ; Friedel-Crafts reaction ; selective ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The para-acylation of calix[4]arene (2), calix[6]arene (3), and calix[8]arene (4) by Friedel-Crafts reaction with a wide variety of acyl chlorides leads to 5-7 in moderate to good yields. Friedel-Crafts reaction of 26,28-dimethoxycalix[4]arene (8) gave products 9 selectively disubstituted in the para-positions of phenol rings.
    Additional Material: 4 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19941270310
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  • 10
    Electronic Resource
    Electronic Resource
    Heterocyclic β-Enamino Esters, 321). Reactions of Aliphatic Diamines and Methylamine with 2-Amino-4,5-dihydro-3-furancarboxylic Esters. Revised Constitutions by 13C NMR Studies (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 622-632 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Heterocyclische β-Enaminoester, 321). Zur Reaktion aliphatischer Diamine und von Methylamin mit 2-Amino-4,5-dihydro-3-furancarbonsäureestern. Revidierte Konstitutionsvorschläge durch 13C-NMR-AnalyseDie 13C-NMR-Spektren der Reaktionsprodukte von 2-Amino-4,5-dihydro-3-furancarbonsäure-ethylestern 3a - e mit Ethylendiamin und 1,3-Diaminopropan wurden vermessen und die Konstitutionen mit Hilfe der Gated Decoupling Technik als 3-(2-Imidazolidinyliden)- bzw. 3-(Hexahydro-2-pyrimidinyliden)dihydro-2(3H)-furanone 1a - i und nicht als Furo[2,3-e]-1,4-diazepinone bzw. Furo[2,3-b][1,5]diazocinone 2a - i gesichert. - 3b - e reagieren mit Methylamin zu einem Gemisch aus E- und Z-Isomeren der 3-[Amino(methylamino)methylen]-4,5-dihydro-2(3H)-furanone 6b - e und 6'b - e. Unabhängig von der Substitution beträgt das E-/Z-Verhältnis ungefähr 40:60.
    Notes: 13C NMR spectra of the reaction products of ethyl 2-amino-4,5-dihydro-3-furancarboxylates 3a - e with ethylenediamine and 1,3-diaminopropane, respectively, were measured, and the constitutions were confirmed with the aid of gated decoupling technique to be 3-(2-imidazolidinylidene)- and 3-(hexahydro-2-pyrimidinylidene)dihydro-2(3H)-furanones 1a - i, instead of furo[2,3-e]-1,4-diazepinones and furo[2,3-b][1,5]diazocinones 2a - i, respectively. - The reaction of 3b - e with methylamine has been studied, and a mixture of E- and Z-isomers of 3-[amino(methylamino)methylene]-4,5-dihydro-2(3H)-furanones 6b - e and 6'b - e has been obtained. The ratios of E- and Z-isomers are approximately 40:60, irrespective of the different substituents.
    Additional Material: 7 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19841170215
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