Über den Verlauf der Indolsynthese nach Emil Fischer

Neber, P. W.; Knöller, Gertrud; Herbst, Klaus‐Dieter; Trissler, A.

doi:10.1002/jlac.19294710106

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Formation Of the New C-c Bond (Stage B)1

Arylhydrazones and Arylhydrazines As Precursors Of Cinnolines1

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1932

2012

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Cited by 25 publications

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“…Intermediate X in the Robinson mechanism has a postulated analogy in the reductive ring contraction of cinnolines to indoles (74,122,160) in which the formation of a similar intermediate (XXIII) is postulated.…”

Section: Formation Of the New C-c Bond (Stage B)mentioning

confidence: 99%

The Fischer Indole Synthesis.

Robinson¹

1963

Chem. Rev.

520

226

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Section: Formation Of the New C-c Bond (Stage B)mentioning

confidence: 99%

The Fischer Indole Synthesis.

Robinson¹

1963

Chem. Rev.

520

226

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“…An example of the production of cinnoline through the formation of the N(2)-C(3) bond is the classical method for the synthesis of 3-hydroxycinnolines-the Neber-Bossel method [33,34]. During the diazotization of (2-aminophenyl)hydroxyacetates and reduction of the diazonium salt the obtained hydrazine undergoes cyclization to 3-hydroxycinnoline when boiled in HCl (Scheme 1).…”

Section: Arylhydrazones and Arylhydrazines As Precursors Of Cinnolinesmentioning

confidence: 99%

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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“…20 Most syntheses of cinnolines involve arenediazonium salts, 21 arylhydrazones, 22 arylhydrazines, 23 and nitriles 24 as their starting materials. Recently, alkynyl-substituted aryltriazene was used as the precursor to prepare cinnoline, 25 however high temperatures or strong acidic conditions were still required.…”

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confidence: 99%