Ueber Cinnolinderivate

Busch, M.; Klett, M.

doi:10.1002/cber.189202502121

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From O-aminophenylpropiolic Acids1

Cyclization Of Arenediazonium Salts1

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1945

2011

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Cited by 14 publications

(6 citation statements)

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“…Distillation of 4-hydroxycinnoline with zinc dust furnished a small amount of a basic oil, which was assumed to be cinnoline. -i -co2 OH S\/\ N This preparation of 4-hydroxycinnoline was repeated by Busch and Klett (11), although in less satisfactory yield than that reported by von Richter. The 4-hydroxycinnoline was converted successfully to cinnoline via the 4-chloro compound by Busch and Rast (12).…”

Section: From O-aminophenylpropiolic Acidsmentioning

confidence: 85%

The Chemistry of Cinnolines.

Leonard¹

1945

Chem. Rev.

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Section: From O-aminophenylpropiolic Acidsmentioning

confidence: 85%

The Chemistry of Cinnolines.

Leonard¹

1945

Chem. Rev.

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“…After decarboxylation of the obtained 4-hydroxycinnoline-3-carboxylic acid 4-hydroxycinnoline was isolated with a quantitative yield [24]. However, attempts to repeat this synthesis by other investigators led to substantially lower yields [65,66]. The formation of the same product as in the Borsche-Herbert method as a result of the Richter cyclization prompted the search for analogies in the mechanisms of these two reactions.…”

Section: Cyclization Of Arenediazonium Saltsmentioning

confidence: 92%

Methods for the synthesis of cinnolines (review)

Vinogradova

Балова

2008

Chem Heterocycl Comp

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This review analyses the principal approaches to the synthesis of the cinnoline nucleus, used as synthetic precursors of arenediazonium salts, arylhydrazones, and arylhydrazines, and also reductive methods for the synthesis of polycondensed derivatives of cinnoline. The mechanisms of the transformations and the possibilities and limitations of the various methods are discussed. Special attention is paid to methods based on the cyclization of derivatives of arenediazonium salts, which have been developed substantially in recent years.

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“…4-Chlorocinnoline was prepared by the procedure of Leonard and Boyd (6). 4-Chlorocinnoline is unstable (5) and thus was prepared in small quantities and used immediately upon purification by recrystallization from petroleum ether (b.p. 30-60°), pale yellow needles melting at 76-76.5°.…”

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confidence: 99%