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• W2171670149 abstract "Aus den 2-Benzopyryliumsalzen 3a–d bildet sich mit überschüssigem Hydrazinhydrat über ein Monohydrazon 11 eine Verbindung der Zusammensetzung C22H26N2O4, die nach den spektroskopischen Daten und chemischen Eigenschaften 5 H-2,3-Benzodiazepin-Struktur (5) besitzt. Aus dem entsprechenden, aliphatische und aromatische Ketogruppen enthaltenden 1,5-Diketon 2 entsteht mit Hydrazinhydrat das Monohydrazon 9 und als Nebenprodukt das stabile Addukt 10. Die Cyclokondensation von 9 zu 5 geht thermisch nur basenkatalysiert, bei Einwirkung von Mineralsäuren dagegen auch bei niedrigeren Temperaturen vor sich, wobei 5·HX entsteht. Die Reaktion von 2 mit H2NNH2·HX in heißem Äthanol liefert gleichfalls 5·HX. Heterocyclic Compounds, I. The First 5H-2,3-Benzodiazepine: Synthesis of 1-(3,4-Dimethoxyphenyl)-5-ethyl-7,8-dimethoxy-4-methyl-5H-2,3-benzodiazepine The 2-benzopyrylium salts 3a–d are converted by means of excess hydrazine hydrate via the monohydrazone intermediate 11 into a substance of the composition C22H26N2O4. According to spectroscopic data as well as to chemical properties the structure 5H-2,3-benzo-diazepine may be assigned to it (5). The 1,5-diketone 2, containing suitable aliphatic and aromatic keto groups, forms, with the help of hydrazine hydrate, the monohydrazone9 and as a by-product the stable adduct 10. The thermal cyclocondensation of 9 into 5 is possible only by means of alkaline catalysis. Mineral acid catalysis again promotes cyclization already at low temperature, resulting in compound 5·HX. Reaction of 2 with H2NNH2·HX in hot ethanol equally furnishes 5·HX." @default.
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• W2171670149 date "1974-12-01" @default.
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• W2171670149 title "Heterocyclische Verbindungen, I. Synthese des ersten 5 <i>H</i> ‐2,3‐Benzodiazepins, des 5‐Äthyl‐1‐(3,4‐ dimethoxyphenyl)‐7,8‐dimethoxy‐4‐methyl‐5‐ <i>H</i> ‐2,3‐benzodiazepins" @default.
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• W2171670149 doi "https://doi.org/10.1002/cber.19741071219" @default.
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