Cinnolines

Aryl diazonium salts occupy a privileged role in synthetic chemistry owing to their ready availability and versatile reactivity. While their applications in accessing diversely functionalized arene derivatives via denitrogenation‐coupling and reduction/addition reactions have been well recognized by practitioners in both academia and industry, recent renaissance in chemical transformations of retaining the key N2‐unit has emerged as a powerful technique to construct various N‐heterocycles. This review covers the history and latest advances in cyclization and cycloaddition reactions using aryl diazonium salts as N2‐annulation synthons. The scope, applications, and opportunities in exploring new chemical space by this sustainable strategy are summarized and discussed.

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Darstellung von 4‐Hydroxycinnolin‐Derivaten mit 3‐ständiger Sulfonsäure‐, Sulfonamid‐ oder Sulfon‐Gruppierung und von 1‐Ethyl‐1,4‐dihydro‐4‐oxocinnolin‐3‐carbonsäuren

Albrecht

1978

Justus Liebigs Ann. Chem.

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Es werden 4-Hydroxycinnolin-Derivate 2 hergestellt, die in 3-Stellung eine Sulfonsaure-, Sulfonamid-, Methylsulfonyl-oder Phenylsulfonyl-Gruppe enthalten, indem ein o-Aminoacetophenon 1 mit der entsprechenden Gruppe in w-Position diazotiert wird. In den 3-Methylsulfonyl-Derivaten 2 wird die I-Stellung ethyliert, die Methylsulfonyl-Gruppe gegen eine Nitrilgruppe ausgetauscht und letztere verseift, wobei l-Ethyl-l,4-dihydro-4-oxocinnolin-3-carbonsauren 9 entstehen. Preparation of 4-Hydroxycinnoline Derivatives with Sulfonic Acid, Sulfonamide or Sulfone Moieties in Position 3 and of l-Ethyl-l,4-dihydro-4oxocinnoline-3-carboxylicAcids 4-Hydroxycinnoline derivatives 2 having a sulfonic acid, sulfonamide, methylsulfonyl or phenylsulfonyl group in position 3 were synthesized by diazotization of an o-aminoacetophenone 1 with the corresponding group in thew position. Position 1 in the 3-methylsulfonyl derivatives 2 is ethylated and the methylsulfonyl group replaced by a cyano group, which is then hydrolyzed, yielding the 1 -ethyl-l,4-dihydro-4-oxocinnoline-3-carboxylic acids 9.

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Cinnolines

Cited by 7 publications

References 212 publications

Addition von Aldehyden an aktivierte Doppelbindungen, XXXII. Synthesen und Reaktionen von 1,4‐Diketoketalen, 1,4,8‐Triketonen und 1,4,9‐Triketonen

Addition von Aldehyden an aktivierte Doppelbindungen, XXXII. Synthesen und Reaktionen von 1,4‐Diketoketalen, 1,4,8‐Triketonen und 1,4,9‐Triketonen

Aryl DiazoniumSalt‐TriggeredCyclization and Cycloaddition Reactions: Past, Present, and Future

Darstellung von 4‐Hydroxycinnolin‐Derivaten mit 3‐ständiger Sulfonsäure‐, Sulfonamid‐ oder Sulfon‐Gruppierung und von 1‐Ethyl‐1,4‐dihydro‐4‐oxocinnolin‐3‐carbonsäuren

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