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  • 1
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 104 (1971), S. 932-940 
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Orthoamides, XVII. Reactions of (Dimethylamino)alkoxyacetonitriles(Dimethylamino)alkoxyacetonitriles (1) react with alcohols to form transacetalisation products. Reaction of 1 with primary amines results in elimination of alcohol and HCN and formation of formamidines (2); reaction of 1 with secondary amines affords aminals of glyoxylonitriles (6, 7). 1 reacts with reactive aldehydes in a multiple-step process to yield the corresponding α-(dimethylamino)nitriles 8 or the corresponding acyloins 9.
    Notes: Dimethylamino-alkoxy-acetonitrile (1) reagieren mit Alkoholen unter Umacetalisierung, mit primären Aminen unter Alkohol- und HCN-Abspaltung zu Formamidinen (2) und mit sekundären Aminen zu Aminalen des Glyoxylsäurenitrils (6, 7). Mit reaktiven Aldehyden entstehen in einer Mehrstufenreaktion die entsprechenden α-Dimethylamino-nitrile 8 oder die entsprechenden Acyloine 9.
    Type of Medium: Electronic Resource
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  • 2
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 104 (1971), S. 924-931 
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Orthoamides, XVI. Syntheses of O. N- and N.N-Acetals of α-Keto Carbonitriles and IminoestersO.N-acetals of α-keto carbonitriles (1) are formed by the reaction of dimethylformamide dialkylacetals with acyl cyanides as well as by the reaction of adducts of dialkylformamide and dimethyl sulfate with sodium cyanide in water. The corresponding N.N-acetals (2) are produced by reaction of 1 with dimethylamine, by reaction of aminalester with acyl cyanide, or by treatment of tetramethylformamidinium methyl sulfate with sodium cyanide in water. N-Alkylcarboxamide dimethyl sulfate adducts (3) react with sodium cyanide in water to give the methyl ester of the corresponding N-alkylcarboximidic acid (5).
    Notes: O.N-Acetale der α-Keto-carbonsäurenitrile (1) entstehen aus Dimethylformamid-dialkyl-acetalen und Acylcyaniden sowie aus Dialkylformamid-Dimethylsulfat-Addukten und Natriumcyanid in Wasser. Die entsprechenden N.N-Acetale (2) entstehen aus 1 mit Dimethylamin bzw. aus Aminalester mit Acylcyaniden oder aus Tetramethylformamidinium-methylsulfat mit Natriumcyanid in Wasser. N-Monoalkylsubstituierte Säureamid-Dimethylsulfat-Addukte (3) bilden mit Natriumcyanid in Wasser N-Alkyl-iminoester (5).
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
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  • 3
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 104 (1971), S. 3475-3485 
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Orthoamides, XIX. Synthesis and Reactions of Substituted Amide AcetalsCarboxamides (1) are alkylated by triethyloxoniumtetrafluoroborate to give the corresponding carbonium tetrafluoroborates (2). As a rule, 2 reacting with sodium ethylate at 0° affords the amide acetals (3). The reaction of 3 with nucleophiles at 80° results in the elimination of ethanol and formation of the aminomethylene compounds.
    Notes: Carbonsäureamide (1) werden mit Triäthyloxonium-tetrafluoroborat zu den entsprechenden Carbonium-tetrafluoroboraten (2) alkyliert, die sich mit Natriumäthylat bei 0° in der Regel zu den Amidacetalen (3) umsetzen lassen. Aus 3 und nukleophilen Substanzen entstehen bei 80° unter Äthanolabspaltung die entsprechenden Aminomethylen-Verbindungen.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
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  • 4
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 105 (1972), S. 2264-2270 
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Orthoamides, XXII. Synthesis and Reactions of O.N-Bis(trimethylsilyl) formamideFormamide reacts with trimethylchlorosilane to give bis(trimethylsilyl) formamide (2). Reaction of 2 with enolisable CH2-active compounds (6-9) results in trimethylsilylethers (13-16) and N-(trimethylsilyl) formamide (20), whereas reaction of 2 with non enolisable CH2-active compounds (10-12) affords aminomethylene compounds (17-19) and hexamethylsiloxane (21).
    Notes: Aus Formamid und Trimethylchlorsilan entsteht Bis-trimethylsilyl-formamid (2). 2 bildet mit enolisierbaren CH2-aktiven Verbindungen (6-9) silylierte Enoläther (13-16) und N-Trimethylsilyl-formamid (20), mit nicht enolisierbaren CH2-aktiven Verbindungen (10-12) Aminomethylen-Verbindungen (17-19) und Hexamethylsiloxan (21).
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
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  • 5
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Durch Umsetzung von N.N-Dialkylformamid-Dialkylsulfat-Addukten mit Alkoholaten in Alkohol oder durch Umacetalisierung einfacher oder gemischter N.N-Dialkylformamid-dialkylacetale mit Alkoholen erhält man N.N-Dialkylformamid-dialkylacetale (Amidacetale); die bei der Umsetzung der N.N-Dialkylformamid-Dialkylsulfat-Addukte mit Dimethylamin erhaltenen N.N.N′.N′.-Tetramethyl-formamidinium-methylsulfate lassen sich mit alkoholfreien Alkoholaten zu den Bis-dimethylamino-alkoxy-methanen (Aminalester) umsetzen.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
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  • 6
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 104 (1971), S. 3711-3713 
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
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  • 7
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 105 (1972), S. 1340-1344 
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Orthoamides, XXI. Reactions of (Dialkylamino)methoxyacetonitriles and Bis(dimethylamino)acetonitrile with Alcoholates. - A New Synthesis for Amide Acetals and Aminal Esters(Dialkylamino)methoxyacetonitriles (1) react with alcoholates to form formamide acetals (2a-e). Reactions of bis(dimethylamino)acetonitrile (4) with alcoholic alcoholates afford further amide acetals 2. 4 reacts with alcoholates in absence of alcohols to yield the corresponding aminal esters 5.
    Notes: Dialkylamino-methoxy-acetonitrile (1) reagieren mit Alkalialkoholaten unter Bildung von Formamidacetalen (2a-e). Aus Bis-dimethylamino-acetonitril (4) und alkoholischen Alkoholaten werden weitere Säureamidacetale 2 erhalten. Die Umsetzung von 4 mit alkoholfreiem Alkoholat liefert die Aminalester 5.
    Additional Material: 4 Tab.
    Type of Medium: Electronic Resource
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  • 8
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Orthoamides, XXXVII. Reactions of 2,2-Bis(dialkylamino)acetonitriles and 2-(Dialkylamino)-2-methoxyacetonitriles with IsocyanatesThe nitriles 1a-c react with isocyanates to give the parabanic acid aminals 10a-g. By alcoholysis of the aminals 10 the parabanic acid O,N-acetals 12a-d are prepared. Compounds of type 12 are also accessible from the amide acetal 3a and 5-imino-2,4-imidazolidinediones 13. By means of the 14C-labelled nitrile 22 it is shown that the C-5 atom of the imidazolidine system in 10 arises from the nitrile group of 1. Hence, the reactions yielding the compounds 10 are mechanistically not related with the reactions of the amide acetals 3 with isocyanates giving parabanic acid O,N-acetals 7. From the complex product mixtures, formed in the reaction of the nitriles 2 with isocyanates, the parabanic acid O,N-acetals 7a-c and the 5-imino-2,4-imidazolidinediones 13a,c are isolated.
    Notes: Die Nitrile 1a-c setzen sich mit Isocyanaten zu den Parabansäure-aminalen 10a-g um. Durch Alkoholyse der Aminale 10 werden die Parabansäure-O,N-acetale 12a-d dargestellt. Verbindungen des Typs 12 entstehen auch bei der Einwirkung des Amidacetals 3a auf 5-Imino-2,4-imidazolidindione 13. Mit Hilfe des 14C-markierten Nitrils 22 wird nachgewiesen, daß das C-5-Atom des Imidazolidinringes von 10 aus der CN-Gruppe von 1 herrührt. Die zu 10 führenden Reaktionen sind daher mechanistisch nicht verwandt mit den Umsetzungen von Amidacetalen 3 mit Isocyanaten, bei denen Parabansäure-O,N-acetale 7 entstehen. Die Nitrile 2 reagieren mit Isocyanaten zu komplexen Produktgemischen, aus denen die Parabansäure-O,N-acetale 7a-c und die 5-Imino-2,4-imidazolidindione 13a,c isoliert werden.
    Additional Material: 1 Tab.
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  • 9
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 104 (1971), S. 3714-3715 
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
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  • 10
    ISSN: 0941-1216
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Orthoamides. LI. Push-Pull-Butadienes and Heterocycles from Alkyne Carboxylic Acid Orthoamides and CH2-acidic CompoundsThe acetylides 4b, 4f react with N,N,N′,N′,N″,N″-hexamethylguanidiniumchloride (5) to give the orthoamides 6b, 6f, resp. From CH2-acidic compounds and the orthoamides 6a, c, e can be obtained the push-pull-substituted butadienes 8a-8aj. The 2,3,5-trimethyl-thiadiazolium salt 9 does not condense with 6e, as other CH2-acidic compounds do, instead the vinylogous guanidinium salt 10a is produced. On heating, the ketenaminals 8d, aa cyclize to give the pyridone-carbonitriles 11a, b, resp. From 4-amino-coumarins 12 and the orthocarboxylic acid amideacetals 13a, b and the ketenaminal 16 resp., the amidines 14a-c and the heterocyclic compounds 15a-c resp., are formed. The enamines 17a-c, 19a, b react with the orthoamides 6a-f to give the pyridine derivatives 18a-1, 20a-h and 21a, b, resp. Analogously, from 6-aminouracil 22 and 6a, b, e, f are formed the pure 7-dimethylaminopyrido[2,3-d] pyrimidines 23a, b or mixtures of compounds 23c, d and the isomeric 4-dimethylamino-pyrido[2,3-d]pyrimidines 24a, b resp., which can be separated via their salts 25a,b/26a,b. The heterocyclic compounds 30a-d, 32a,b can be prepared from the pyrazole derivatives 28, 31 resp. and the orthoamides 6a-f.
    Type of Medium: Electronic Resource
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