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  • Springer  (11)
  • 1965-1969  (11)
  • 1966  (11)
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  • 1965-1969  (11)
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  • 1
    Electronic Resource
    Electronic Resource
    Springer
    Monatshefte für Chemie 97 (1966), S. 409-416 
    ISSN: 1434-4475
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Abstract o-Aminophenylglyoxal-dimethylacetal (1) has been condensed with several cyclic ketones, acetophenones, and with acetone to yield derivatives of quinoline-4-aldehyde.1 reacts with ethyl acetoacetate and diethyl malonate at 160° yielding 3-acetyl-(11) and 3-carbethoxy-4-dimethoxymethyl-carbostyril (12) respectively. o-Acetaminophenylglyoxal dimethyl acetal (21) undergoes ring closure to carbostyril-4-aldehyde dimethyl acetal (22), when treated with sodium ethoxide; the reaction of21 with ethyl cyanoacetate leads to 3-cyano-4-dimethoxymethyl-carbostyril (24).
    Notes: Zusammenfassung o-Aminophenylglyoxal-dimethylacetal (1) läßt sich mit Carbonylverbindungen, die eine α-Methylengruppe enthalten, im Sinne einerFriedländer-Synthese zu Derivaten des Chinolin-4-aldehyds umsetzen. Bei 150–160° reagiert1 mit Acetessigester und Malonester unter Bildung des 3-Acetyl-(11) bzw. 3-Car-bäthoxy-4-dimethoxymethyl-carbostyrils (12). o-Acetaminophenylglyoxal-dimethylacetal (21) kann mit Na-Äthylat zum Carbostyril-4-aldehyd-dimethylacetal (22) cyclisiert werden; mit Cyanessigester kondensiert sich21 zum 3-Cyan-4-dimethoxy-methyl-carbostyril (24).
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  • 2
    Electronic Resource
    Electronic Resource
    Springer
    Monatshefte für Chemie 97 (1966), S. 391-397 
    ISSN: 1434-4475
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Abstract 3-Phenylazo-4-hydroxy-2-oxo-indeno[1,2-b]pyran (4) is hydrolysed by heating in aqueous sodium hydroxide solution to 3′-hydroxyindenyl-(2′)-glyoxal-2-phenylhydrazone (11). This compound reacts with phenylhydrazine under ring closure to 1,4-dihydro-1-phenylindeno[1,2-c]pyrazol-(3)-aldehyde phenylhydrazone (21).
    Notes: Zusammenfassung 3-Phenylazo-4-hydroxy-2-oxo-indeno[1,2-b]pyran (4) läßt sich durch Erhitzen mit verd. Lauge zum 3′-Hydroxyindenyl-(2′)-glyoxal-2-phenylhydrazon (11) hydrolysieren, welches mit Phenylhydrazin unter Ringschluß zum 1,4-Dihydro-1-phenylindeno-[1,2-c]pyrazol-(3)-aldehydphenylhydrazon (21) reagiert.
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  • 3
    Electronic Resource
    Electronic Resource
    Springer
    Monatshefte für Chemie 97 (1966), S. 10-18 
    ISSN: 1434-4475
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Abstract Monosubstituted malonyl chlorides react with nitriles and isocyanates to 1.3-oxazines. Malonyl chloride itself reacts with nitriles, isocyanates, and iso-thiocyanates in a complicated manner yielding bicyclic pyrono-1.3-oxazines.
    Notes: Zusammenfassung Monosubstituierte Malonsäurechloride reagieren mit Nitrilen bzw. Isocyanaten zu 1,3-Oxazinen1. Malonylchlorid setzt sich mit den gleichen Reaktionspartnern sowie mit Phenylsenföl in einer komplizierteren Reaktionsfolge zu bicyclischen Pyrono-1,3-oxazinen1–3 um.
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  • 4
    Electronic Resource
    Electronic Resource
    Springer
    Monatshefte für Chemie 97 (1966), S. 398-408 
    ISSN: 1434-4475
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Abstract 1,3-Dicarbonyl compounds react with C3O2 in the presence of catalytic amounts of H2SO4 to derivatives of 4-hydroxy-2H,5H-pyrano[4,3-b]pyran-2,5-dione. The mechanism of the reaction, the structure, IR-, UV- andNMR-spectra are discussed.
    Notes: Zusammenfassung 1,3-Dicarbonylverbindungen reagieren mit Kohlensuboxid (C3O2) in Gegenwart katalyt. Mengen konz. H2SO4 zu Derivaten des 4-Hydroxy-2H,5H-pyrano[4,3-b]pyran-2,5-dions. Reaktionsverlauf, Struktur, IR-, UV- undNMR-Spektren werden diskutiert.
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  • 5
    Electronic Resource
    Electronic Resource
    Springer
    Monatshefte für Chemie 97 (1966), S. 710-715 
    ISSN: 1434-4475
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Abstract The reaction of benzoylacetone with malonylchloride yields according toButt andElvidge 1 5-acetyl-4-hydroxy-6-phenyl-2-pyrone, wich is isomerised at 168° to an isomeric compound with a m. p. of 220°. However the physical properties of these two products are not in agreement with the previously1 postulated simple keto-enol-tautomerism between these compounds.
    Notes: Zusammenfassung NachButt undElvidge 1 reagiert Benzoylaceton mit Malonylchlorid zu 4-Hydroxy-5-acetyl-6-phenyl-pyron-(2) (Schmp. 168°), welches beim Erhitzen auf 168° ein Isomeres vom Schmp. 220° gibt. Die Formulierung dieser beiden Verbindungen als Keto-Enol-Tautomere wird auf Grund verschiedener physikalischer Daten widerlegt.
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  • 6
    Electronic Resource
    Electronic Resource
    Springer
    Monatshefte für Chemie 97 (1966), S. 1131-1133 
    ISSN: 1434-4475
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Abstract The assignment of the infrared absorption bands in the 1700–1500 cm−1 region has been tried for a number of oximes of aromatic ketones.
    Notes: Zusammenfassung Es wird der Versuch unternommen, die bei den Oximen aromatischer Chinone im Doppelschwingungsbereich auftretenden Banden zuzuordnen.
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  • 7
    Electronic Resource
    Electronic Resource
    Springer
    Monatshefte für Chemie 97 (1966), S. 1207-1216 
    ISSN: 1434-4475
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Abstract Betaine reacts with phenol and alkyl or halogen substituted phenols in the presence of CaO in good yield to phenyl methyl ethers and phenoxy acetic acids. Also phenols with steric hindrance are readily converted in methyl ethers. Various reaction pathways are discussed.
    Notes: Zusammenfassung Betain reagiert mit Phenol und seinen Alkyl- bzw. Halogenderivaten in Gegenwart von Calciumoxid in guten Ausbeuten zu Phenylmethyläthern und Phenoxyessigsäuren. Auch sterisch gehinderte Phenole lassen sich leicht in die Methyläther überführen. Verschiedene Reaktionswege werden diskutiert.
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  • 8
    Electronic Resource
    Electronic Resource
    Springer
    Monatshefte für Chemie 97 (1966), S. 77-86 
    ISSN: 1434-4475
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Abstract 3-Amino-4-hydroxycoumarin (4), obtained in 92% yield by the catalytic hydrogenation of 3-phenylazo-4-hydroxycoumarin (1), is readily converted by refluxing in 2N-NaOH to 3,6-bis-(2-hydroxyphenyl)-2.5-dihydropyrazine (10). The dehydrogenation of10 with a Pd catalyst yields the corresponding pyrazine14, which can also be obtained from the o-hydroxyphenylglyoxal-phenylhydrazone (13). The reduction of10 with sodium in butanol yields the known 2.5-bis(2-hydroxyphenyl)-piperazine (18); the reaction of10 with acetic anhydride leads by isomerization to the 1,4-diacetyl-3,6-bis(2-acetoxyphenyl)-1.4-dihydropyrazine (17).
    Notes: Zusammenfassung 3-Amino-4-hydroxycumarin (4), welches durch katalyt. Reduktion von 3-Phenylazo-4-hydroxycumarin (1) in 92proz. Ausb. zugänglich ist, wird beim Erhitzen mit 2n-NaOH in 3,6-Bis-(2-hydroxyphenyl)-2,5-dihydropyrazin (10) übergeführt. Die Dehydrierung von10 mit Pd liefert das entsprechende Pyrazin14, das auch aus dem o-Hydroxyphenylglyoxal-phenylhydrazon (13) gewonnen werden kann. Die Reduktion von10 mit Na/Butanol führt zum Piperazin18, die Reaktion mit Ac2O zum 1,4-Dihydropyrazinderivat17.
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  • 9
    Electronic Resource
    Electronic Resource
    Springer
    Monatshefte für Chemie 97 (1966), S. 1046-1052 
    ISSN: 1434-4475
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Abstract The isomeric compounds1 4-hydroxy-5-acetyl-6-phenyl-pyron-2 (1) and 4-hydroxy-5-benzoyl-6-methyl-pyron-2 (2) yield 5-benzoyl-dehydroacetic acid (3) if with glacial acetic acid and POCl3. In contrast to dehydroacetic acid2 5-benzoyl-dehydroacetic acid (3) reacts in ethanolic HCl to 2,6-dimethyl-3-carbethoxy-5-benzoyl-pyron-(4) (6). However, with aquenous HCl3 is converted to 2.6-dimethyl-5-benzoyl-pyron-(4) (5).
    Notes: Zusammenfassung Die vonButt undElvidge aufgefundenen Isomeren, 4-Hydroxy-5-acetyl-6-phenyl-pyron-(2) (1) und 4-Hydroxy-5-ben-zoyl-6-methyl-pyron-(2) (2), ergeben bei der Umsetzung mit POCl3 und Eisessig 5-Benzoyl-dehydracetsäure (3). Im Gegensatz zur Dehydracetsäure2 reagiert 5-Benzoyl-dehydracetsäure (3) in alkohol. HCl zum 2,6-Dimethyl-3-äthoxycarbonyl-5-benzoyl-pyron-(4) (6). Die Struktur dieser Verbindung wird auf chemischem und physikalischem Wege abgeleitet. Mit wäßr. HCl läßt sich3 in 2,6-Dimethyl-5-benzoyl-pyron-(4) (5) umwandeln.
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  • 10
    Electronic Resource
    Electronic Resource
    Springer
    Monatshefte für Chemie 97 (1966), S. 1391-1393 
    ISSN: 1434-4475
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Abstract The anils of cyclanones react with oxalyl chloride yielding 1-phenyl-4,5-polymethylene-pyrrol-2,3-dion.
    Notes: Zusammenfassung Cyclanon-anile reagieren mit Oxalylchlorid in einfacher Weise zu 1-Phenyl-4,5-polymethylen-2,3-dion-pyrrolen.
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