Bredereck-Gompper synthesis

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The Bredereck-Gompper synthesis is a name reaction in organic chemistry. It was first described in 1956 by the German chemists Hellmut Bredereck (1904–1981) and Rudolf Gompper (1926–1999). It is used for the synthesis of 4,6-disubstituted pyrimidines .

Overview reaction

This reaction allows 4,6-dialkylpyrimidines to be synthesized starting from a 1,3-dicarbonyl compound (R 1 , R 2 = alkyl) .

Overview reaction of the Bredereck-Gompper synthesis

Reaction mechanism

Bredereck-Gompper synthesis - reaction mechanism

In the proposed reaction mechanism, the diketone 1 , which is in keto-enol equilibrium with the enol form, reacts with formamide to form 2 with dehydration . Enamine 3 is formed by adding water and splitting off formic acid . If there is another reaction with formamide and two water molecules are split off, the 4,6-dialkylpyrimidine 4 is formed .

variants

The synthesis of 4- or 5-monosubstituted pyrimidine derivatives can also take place analogously to the above mechanism. The reaction of the diketone with tris (dimethylamino) methane also results in the formation of 4-substituted and 4,5-disubstituted pyrimidines.

Individual evidence

  1. ↑ H. Bredereck, R. Gompper, G. Morlock: New pyrimidine synthesis from beta-dicarbonyl compounds and formamide . In: Angewandte Chemie, 1956, Vol. 68, No. 4, p. 151, https://doi.org/10.1002/ange.19560680404 .
  2. ↑ a b c Eberhard wide Maier, Günther Jung: Organic Chemistry: Fundamentals, classes of compounds, reactions, concepts, molecular structure, natural products, synthetic planning, sustainability Vol 7. Georg Thieme Verlag, Stuttgart, 2012, p 688. ISBN 978-3-13 -541507-9 .
  3. ↑ Entry on Bredereck-Gommper synthesis. In: Römpp Online . Georg Thieme Verlag, accessed on April 8, 2020.
  4. ↑ Hellmut Bredereck, Rudolf Gompper, Gerhard Morlock: Foormamid reactions, VIII. A new pyrimidine synthesis. In: Chemischeberichte, 1957, Vol. 90, No. 6, pp. 942–952, https://doi.org/10.1002/cber.19570900613 .
  5. ↑ Hellmut Bredereck, Rudolf Gompper, Gerhard Morlock: Foormamid reactions, X. Pyrimidines from acetylene ketones and formamide . In: Chemischeberichte, 1958, Vol. 91, No. 12, pp. 2830–2849, https://doi.org/10.1002/cber.19580911239 .
  6. ↑ Hellmut Bredereck, Rudolf Gompper, Bernd Geiger: acid amide reactions, XXII. Synthesis of pyridines using trisformaminomethane . In: Chemischeberichte, 1960, Vol. 93, No. 6, pp. 1402-1406, https://doi.org/10.1002/cber.19600930626 .