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Gewald reaction information


Gewald reaction
Named after Karl Gewald
Reaction type Ring forming reaction
Identifiers
Organic Chemistry Portal gewald-reaction

The Gewald reaction is an organic reaction involving the condensation of a ketone (or aldehyde when R2 = H) with a α-cyanoester in the presence of elemental sulfur and base to give a poly-substituted 2-amino-thiophene.[1][2]

The Gewald reaction
The Gewald reaction

The reaction is named after the German chemist Karl Gewald (born 1930).[3][4][5]

  1. ^ Gewald, K.; Schinke, E.; Böttcher, H. Ber. 1966, 99, 94-100.
  2. ^ Sabnis, R. W. Sulfur Rep. 1994, 16, 1-17. (Review)
  3. ^ John A. Joule, Keith Mills: Heterocyclic Chemistry, John Wiley & Sons, 5. Auflage (2010), p. 340, ISBN 978-1-4051-3300-5.
  4. ^ Bradford P. Mundy, Michael G. Ellerd, Frank G. Favaloro, Jr.: Name Reactions and Reagents in Organic Synthesis, John Wiley & Sons, 2. Auflage (2005) p. 306, ISBN 0-471-22854-0.
  5. ^ Christopher Hume: Applications of Multicomponent Reactions in Drug Discovery – Lead Generation to Process Development, p. 311−341, see p. 332−334, In Jieping Zhu, Huges Bienaymé: Multicomponent Reactions, Wiles-VCH Verlag, 2005, ISBN 978-3-527-30806-4.

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Gewald reaction

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The Gewald reaction is an organic reaction involving the condensation of a ketone (or aldehyde when R2 = H) with a α-cyanoester in the presence of elemental...

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Ring forming reaction

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Knoevenagel condensation

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Malononitrile

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preparation of CS gas: Malononitrile is a suitable starting material for the Gewald reaction, where the nitrile condenses with a ketone or aldehyde in the presence...

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Gattermann aldehyde synthesis Gattermann Koch reaction Gattermann reaction Geminal halide hydrolysis Gewald reaction Gibbs phthalic anhydride process Gilman...

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Thiophene

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similarly using Lawesson's reagent as the sulfidizing agent, or via the Gewald reaction, which involves the condensation of two esters in the presence of elemental...

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Cyanamide

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authors list (link). Gewald, K.; Spies, H.; Mayer, R. (1970). "Zur Reaktion von Enaminen mit Schwefel und Cyanamid" [On the Reaction of Enamines with Sulfur...

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Maxwell Zeb Shumba

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Friedrich Asinger

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University of Halle-Wittenberg, and Karl Gewald, who is best known for the development of the Gewald reaction and his work in the field of thiophenes and...

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