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  • Inorganic Chemistry  (10)
  • 1970-1974  (10)
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  • 1
    Electronic Resource
    Electronic Resource
    Zur Darstellung von 1-Oxo-1.3.6.7-tetrahydro-5H-furo[3.4-b]-pyranen und -thiopyranen (1971)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 104 (1971), S. 734-738 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthesis of 1-Oxo-1.3.6.7-tetrahydro-5H-furo[3.4-b]pyrans and -thiopyransVarious 2-methyl-3-ethoxycarbonyl-5.6-dihydro-4H-pyrans and -thiopyrans (1) react with bromine to form the corresponding 2-bromomethyl derivatives (2), which can be converted by heating to α.β-unsaturated γ-lactones (3) l. r. and n. m. r. spectra are reported and discussed.
    Notes: Die Bromierung verschiedener 2-Methyl-3-äthoxycarbonyl-5.6-dihydro-4H-pyrane und -thiopyrane (1) führt zu den entsprechenden 2-Brommethylverbindungen (2), die thermisch zu α.β-ungesättigten γ-Lactonen (3) cyclisiert werden können. Die Strukturen werden durch NMR- und IR-Spektren bewiesen.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19711040310
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  • 2
    Electronic Resource
    Electronic Resource
    Zur Hydrierung von Δ2-5-Isoxazolonen (1973)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 106 (1973), S. 332-338 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: On the Hydrogenation of Δ2-5-IsoxazolonesThe Δ2-5-isoxazolones 1, 5, 8a-c, and 11a, b are opened under conditions of the catalytic reduction to yield β-enamino-β'-ketocarboxylic acids 6a, b. In a second step, the derivatives 8a-c, 11a, b form diazepines 10a-c and pyrazoles 12, 13 by intramolecular cyclization. The structures are elucidated on the basis of the n.m.r. and i.r. spectra.
    Notes: Die Δ2-5-Isoxazolone 1, 5, 8a-c und 11a, b werden bei der katalytischen Hydrierung unter reduktiver Ringöffnung zu β-Enamino-β'-ketocarbonsäuren 6a, b gespalten Dabei cyclisieren die Derivate 8a-c, 11a, b intramolekular zu den Diazepinen 10a-c und Pyrazolen 12, 13. Die Strukturen werden durch NMR- und IR-Spektren bewiesen.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19731060136
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  • 3
    Electronic Resource
    Electronic Resource
    Heterocyclische Dicarbonsäureester, II. Zur Reaktion von 2,3-Bis(methoxycarbonyl)-4,5-dihydrofuranen mit Hydrazin und 1,2,3,6-Tetrahydropyridazin.  -  Synthese von 3-Hydroxy-4-(2-hydroxyalkyl)-5-pyrazolcarbonsäure-Derivaten (1973)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 106 (1973), S. 1099-1106 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Heterocyclic Dicarboxylic Acid Esters, II. Reaction of 2,3-Bis(methoxycarbonyl)-4,5-dihydrofurans with Hydrazine and 1,2,3,6-Tetrahydropyridazine.  -  Synthesis of 3-Hydroxy-4-(2-hydroxyalkyl)-5-pyrazolcarboxylic Acid DerivativesIn contrast to the 5,6-dihydro-4H-pyran and furan dicarboxylic acid esters 1 and 4, 2,3-bis-(methoxycarbonyl)-4,5-dihydrofurans 10a-c upon treatment with hydrazine do not yield the dihydrazides but undergo ring cleavage to the 3-hydroxy-4-(2-hydroxyalkyl)-5-pyrazolecarboxylic acid hydrazides 11a-c. Under mild conditions the intermediate ester 12a can be isolated. 12a as well as 11a, c can be hydrolyzed to the carboxylic acids 14a, b. Acyllactone rearrangement of the α-alkoxalyllactones 9a, d with hydrazine also yields the esters 12a, b. I.r. and n.m.r. data are discussed.
    Notes: Bei der Behandlung der 2,3-Bis(methoxycarbonyl)-4,5-dihydrofurane 10a-c mit überschüssigem Hydrazinhydrat entstehen, im Gegensatz zum Verhalten der analogen 5,6-Dihydro-4H-pyran- und Furandicarbonsäureester 1 und 4, nicht die entsprechenden Dihydrazide, sondern es tritt Ringöffnung zu den 3-Hydroxy-4-(2-hydroxyalky)-5-pyrazolcarbonsäure-hydraziden 11a-c ein. Unter schonenden Bedingungen läßt sich der 5-Pyrazolcarbonsäureester 12a isolieren. Sowohl 12a als auch 11a, c lassen sich zu den Carbonsäuren 14a, b verseifen. Die Ester 12a, b entstehen ebenfalls in einer Acyllacton-Umlagerung der α-Alkoxalyl-lactone 9a, d mit Hydrazin. Die IR- und NMR-Daten der dargestellten Verbindungen werden diskutiert.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19731060407
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  • 4
    Electronic Resource
    Electronic Resource
    Heterocyclen aus Lactonen, Lactamen und Thiollactonen, XV. Zur Reaktion von α-Acyl- und α-Alkoxyäthyliden-Δβ,γ-butenoliden mit Amidinen, Guanidinen und Hydrazinen (1973)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 106 (1973), S. 874-881 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Heterocycles from Lactones, Lactams and Thiollactones, XV. On the Reaction of α-Acyl- and α-Alkoxyethyliden-Δβ,γ-butenolides with Amidines, Guanidines and HydrazinesThe α-acyl-Δβ,γ-butenolides 2a, b react with amidines, guanidines or hydrazines to give only the enolates 3a-e. The enol ethers 4a-c of the butenolides 2a, b, however, react with amidines as well as guanidines to yield 5-phenacyl- or 5-acetonyl-6-pyrimidones 6a-n and with hydrazines to give 5-phenacyl-5-pyrazolones 7a, b. The thermally instable 6-pyrimidones 61-n readily cyclize to the furo[2,3-d]pyrimidines 8a-c. The structures of the compounds are confirmed by their n.m.r. and i.r. spectra.
    Notes: Mit Amidinen, Guanidinen oder Hydrazinen reagieren die α-Acyl-Δβ,γ-butenolide 2a, b nur zu den Enolaten 3a-e. Dagegen bilden die Enoläther 4a-c der α-Acylbutenolide mit Amidinen sowie Guanidinen unter Lactonringöffnung 5-Phenacyl- bzw. 5-Acetonyl-6-pyrimidone 6a-n und mit Hydrazinen die entsprechenden 5-Pyrazolone 7a, b. Von den 6-Pyrimidonderivaten cyclisieren 61-n spontan oder bereits unter milden Bedingungen zu den Furo[2,3-d]pyrimidinen 8a-c. Die IR- und NMR-Spektren der erhaltenen Verbindungen werden beschrieben.
    Additional Material: 8 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19731060318
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  • 5
    Electronic Resource
    Electronic Resource
    Heterocyclische Dicarbonsäureester, I. Zur Synthese und Reaktivität von 2-Methyl-3,4-dihydro-2H-pyrano[2,3-d]pyridazinen (1973)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 106 (1973), S. 929-934 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Heterocyclic Dicarboxylic Acid Esters, I. Synthesis and Reactivity of 2-Methyl-3,4-dihydro-ZH-pyrano[2,3-d]pyridazines6-Methyl-2,3-bis(methoxycarbonyl)-5,6-dihydro-4H-pyrane (2a) reacts with hydrazine to give the dihydrazid 3 which can be converted to 2-niethyl-3,4,5,6,7,8-hexahydro-2H-pyrano [2,3-d]-pyridazine-5,8-dione (4) under elimination of hydrazine. Treatment of 4 with POCl3/pyridine yields the 5,8-dichloropyranopyridazine 5. The reactivity of this compound to nucleophilic agents is studied and discussed. I. r. and n. m. r. data are given.
    Notes: 6-Methyl-2,3-bis(methoxycarbonyl)-5,6-dihydro-4H-pyran (2a) setzt sich mit Hydrazinhydrat zum Dihydrazid 3 um, welches unter Hydrazinabspaltung in das 2-Methyl-3,4,5,6,7,8-hexahydro-2H-pyrano[2,3-d]pyridazin-5,8-dion (4) übergeht. Durch Behandlung von 4 mit POCl3/Pyridin erhält man das 5,8-Dichlorpyranopyridazin 5, dessen Reaktivität gegenüber nucleophilen Agentien untersucht und diskutiert wird. Die IR- und NMR-Daten der erhaltenen Verbindungen werden aufgeführt.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19731060325
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  • 6
    Electronic Resource
    Electronic Resource
    Heterocyclen aus Lactonen, Lactamen und Thiollactonen, 16. Über die Synthese heterokondensierter Pyrimidine aus 4-Chlor-5-acylpyrimidinen (1973)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 106 (1973), S. 3524-3532 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Heterocyclic Compounds from Lactones, Lactams, and Thiollactones, 16. Synthesis of Heterocondensed Pyrimidines from 4 Chloro-5-acylpyrimidines4-Chloro-5-acylpyrimidines (1a - c) react according to the scheme pyrimidine-δ⊕C4-C5-Cδ⊕ + N—C—N, + N—C—C—N, + N—C—C—S, and + N—C—C -O to yield the following heterocondensed systems: pyrimido[4,5-d]pyrimidines (8a-h), pyrido[3,2-b]pyrimido[4,5-e]-[1,4]diazepine (6), pyrimido[4,5-b][1,5]benzothiazepines (13a, c) and -[1,5]benzoxazepines (17a- c) as well as pyrimido[5′,4′:5,6]pyrimido[l,2-a]benzimidazoles (16a-c). The u.v., i.r., and n.m.r. spectra of these ring systems are described.
    Notes: 4-Chlor-5-acylpyrimidine (1a-c) reagieren nach dem Schema: Pyrimidin-δ⊕C4—C5—;Cδ⊕ + N—C—N, + N—C—C—N, + N—C—C—S und + N—C—C—O zu den folgenden kondensierten heterocyclischen Systemen: Pyrimido[4,5-d]pyrimidine (8a-h), Pyrido[3,2-b]-pyrimido[4,5-e][1,4]diazepin (6), Pyrimido[4,5-b][1,5]benzothiazepine (13a, c) und -[1,5]-benzoxazepine (17a - c) sowie Pyrimido[5′,4′: 5,6]pyrimido[1,2-a]benzimidazole (16a - c). Die UV-, IR- und N M R-Spektren dieser Ringsysteme werden beschrieben.
    Additional Material: 8 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19731061108
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  • 7
    Electronic Resource
    Electronic Resource
    Zur Synthese von substituierten Buten-(2)-oliden-(4.1) und 3-Amino-1-methyl-Δ3-pyrrolon-(2) (1971)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 104 (1971), S. 2458-2466 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: On the Synthesis of Substituted 2-Buten-4-olides and 3-Amino-1-methyl-3-pyrrolin-2-oneα-Azido-γ-lactones (2a-c) in ethanol eliminate with catalytic amounts of sodium ethoxide 1 mole of nitrogen and rearrange to yield 2-amino-2-buten-4-olides (5a-c). Analogously, 3-azido-1-methyl-2-pyrrolidone (7d) is converted into 3-amino-1-methyl-3-pyrrolin-2-one (8d). Under these conditions α-benzylidenamino-γ-lactone 11a undergoes rearrangement to give 2-benzylamino-2-buten-4-olide 14.
    Notes: α-Azido-γ-lactone (2a-c) eliminieren in Äthanol mit katalytischen Mengen Natriumäthylat Stickstoff und lagern sich in die 2-Amino-buten-(2)-olide-(4.1) 5a-c um. Entsprechend entsteht aus 3-Azido-1-methyl-pyrrolidon-(2) (7d) das 3-Amino-1-methyl-Δ3-pyrrolon-(2) (8d). Das α-Benzylidenamino-γ-lacton 11a lagert unter diesen Bedingungen in das 2-Benzyl-amino-buten-(2)-olid-(4.1) 14 um.
    Additional Material: 9 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19711040815
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  • 8
    Electronic Resource
    Electronic Resource
    Zur Synthese von 1-Oxo-2-alkyl-1.2.3.5.6.7-hexahydropyrrolo[3.4-b]pyranen und -thiopyranen (1972)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 105 (1972), S. 1345-1349 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthesis of 2-Alkyl-1-oxo-1.2.3.5.6.7-hexahydro-pyrrolo[3.4-b]pyrans and -thiopyransThe 2-bromomethyl-3-ethoxycarbonyl-5.6-dihydro-4H-pyrans and -thiopyrans 2 react with primary or secondary amines to give the thermally instable 2-alkylaminomethyl products 4 which undergo cyclization to the α,β-unsaturated γ-lactams 5. The structures are elucidated on the basis of the n.m.r. and i.r. spectra.
    Notes: Die 2-Brommethyl-3-äthoxycarbonyl-5.6-dihydro-4H-pyrane und -thiopyrane 2 reagieren mit primären oder sekundären Aminen über die thermisch instabilen 2-Alkylaminomethyl-Produkte 4 unter Cyclisierung zu α,β-ungesättigten γ-Lactamen 5. Die Strukturen werden durch NMR- und IR-Spektren bewiesen.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19721050425
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  • 9
    Electronic Resource
    Electronic Resource
    Zur Synthese von 1,3-Dimercaptobenzolen aus Resorcinen über die Newman-Kwart-Umlagerung (1973)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 106 (1973), S. 2419-2426 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthesis of 1,3-Dimercaptobenzenes from Resorcins by the Newman-Kwart RearrangementResorcin and its substituted derivatives 3b-d, 7a and b react with dimethylthiocarbamoyl chloride to the O-aryl thiocarbamates 5a-d, 8a and b. At higher temperature these O-aryl esters yield by the Newman-Kwart rearrangement S-aryl thiocarbamates 10a-c, 11a and b, which on alkaline hydrolysis yield the mercapto- and 1,3-dimercaptobenzenes 12a-e.
    Notes: Resorcin und seine substituierten Derivate 3b-d, 7a und b werden mit Dimethylthiocarbamoylchlorid zu den entsprechenden Thiocarbamidsäure-O-arylestern 5a-d, 8a und b umgesetzt. Bei höherer Temperatur isomerisieren diese O-Arylester - in der sogenannten Newman-Kwart-Umlagerung - zu den Thiocarbamidsäure-S-arylestern 10a-c, 11a und b, deren anschließende alkalische Hydrolyse die Mercapto- und 1,3-Dimercaptobenzole 12a-e liefert.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19731060802
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  • 10
    Electronic Resource
    Electronic Resource
    Zur Synthese von Phenanthridinonen-(6) aus 3.4-disubstituierten Cumarinen und ihre Reaktion mit Methylmagnesiumjodid zu Phenanthridiniumjodiden (1973)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 106 (1973), S. 62-68 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: The Synthesis of Phenanthridin-6-ones from 3.4-Disubstituted Coumarins and their Reaction with Methylmagnesium Iodide to Phenanthridinium IodidesThe reaction of ammonia or amines with several 3.4-disubstituted coumarins (5, 6) yields phenanthridin-6-ones 7a-d and 8a-e. Methylmagnesium iodide reduces the 5-methylphenanthridin-6-ones 7b, d, 8c, and 13 to 5.6-dimethylphenanthridinium iodides (11, 12, 15). In addition 13 yields the 5.6.6-trimethylphenanthridine derivative (14) Spectroscopic data are given for all compounds described.
    Notes: Phenanthridinone-(6) 7a-d und 8a-e werden durch Reaktion von Ammoniak oder Aminen mit bestimmten 3.4-disubstituierten Cumarinen (5,6) erhalten. Mit Methylmagnesiumjodid setzen sich die 5-Methyl-phenanthridinone-(6) 7b, d, 8c und 13 zu 5.6-Dimethylphenanthridiniumjodiden (11, 12, 15) um, nur aus 13 entstand auch das 5.6.6-Trimethylphenanthridinderivat (14). Die IR- und NMR-Spektren der erhaltenen Verbindungen werden beschrieben.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19731060110
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