Английская Википедия:Cyanomethine

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Шаблон:Chembox Cyanomethine (4-amino-2,6-dimethylpyrimidine) is an amino and methylated derivative of pyrimidine with the chemical formula Шаблон:Chem2, belonging to a class named cyanalkines.[1]

Properties and synthesis

Cyanomethine is a strongly basic[2] colourless to white crystalline solid. It is soluble in water and slightly soluble in alcohol.[3] It is prepared by the trimerisation of acetonitrile with sodium or potassium,[4] with the corresponding metal cyanide and Шаблон:Chem2 (possibly 2-methylimidazole or 3-methylpyrazole; iminoacetonitrile has been identified[5]) as the main byproducts.[6] It can also made by reaction of sodium methoxide and acetonitrile.[1]

The correspondence of the three acetonitrile units to a tautomer of cyanomethine is:

Файл:Acetonitrile trimerization formal cyanomethine.png

At higher pressure, sodium methoxide instead catalyzes trimerization to form 2,4,6-Trimethyl-1,3,5-triazine.[7]

2,6-Diethyl-5-methyl-4-pyrimidinamine (cyan(o)ethine) is an analogous structure that can be made by trimerization of propionitrile.[1]

Cyanomethine can form complexes with platinum(II) and platinum(IV) compounds.[8]

References

Шаблон:Reflist

  1. 1,0 1,1 1,2 Polymerisation of Nitriles, Journal of the Chemical Society. (1890). United Kingdom: Chemical Society.page 1158
  2. Karrer, P. (1950). Organic Chemistry. page 819
  3. Roscoe, H. E. (1881). A Treatise on chemistry volume 3, 1881.page 523-524
  4. Miller, W. A., McLeod, H. (1880). Elements of Chemistry: Theoretical and Practical, page 174
  5. Derivatives of Hydrocyanic Acid. Competition Science Vision. Jan 2001 page 1494
  6. Methyl cyanide, Thorpe, T. E. (1895). A Dictionary of Applied Chemistry. United Kingdom: Longmans. page 575
  7. T. L. Cairns, A. W. Larchar, and B. C. McKusick, The Trimerization of Nitriles at High Pressures, J. Am. Chem. Soc. 1952, 74, 22, 5633–5636 Publication Date: November 1, 1952 [1]
  8. Kovala-Demertzi, D. Platinum(II) and platinum(IV) complexes of 2-amino-4,6-dimethylpyrimidine. Transition Met Chem 15, 23–26 (1990). https://doi.org/10.1007/BF01032225