Chemistry of 2-aryl-substituted 3-hydroxypyridines

Communication 2. Aminomethylation of 2-(4′-methoxyphenyl)-and 2-(4′-hydroxyphenyl)-3-hydroxypyridines
  • L. D. Smirnov
  • V. I. Kuz'min
  • V. P. Lezina
  • K. M. Dyumaev
Organic and Biological Chemistry
  • 21 Downloads

Conclusions

  1. 1.

    A study was made of the aminomethylation of the 2-(4′-methoxyphenyl)- and 2-(4′-hydroxyphenyl)-3-hydroxypyridines.

     
  2. 2.

    Based on the data of the NMR and IR spectra the amino methylation of 2-(4′-methoxyphenyl)-3-hydroxypyridine is directed to theβ-pyridol ring with the initial formation of the 6-mono- and then the 4,6-bis-Mannich bases; attempts to introduce the dialkylaminomethyl group into the anisole ring proved unsuccessful.

     
  3. 3.

    The aminomethylation of 2-(4′-hydroxyphenyl)-3-hydroxypyridine is initially directed to the phenol ring with the formation of the ortho- and then the di-ortho- derivatives, and only after this to theβ-pyridol ring, with successive substitution in the 6 and then in the 4 position of the pyridine ring.

     

Keywords

Methylation Phenol Pyridine Methoxyphenyl Hydroxyphenyl 

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Literature cited

  1. 1.
    L. D. Smirnov, V. I. Kuz'min, L. N. Mikhailov, V. P. Lezina, and K. M. Dyumaev, Izv. Akad. Nauk SSSR, Ser. Khim., 1845 (1970).Google Scholar
  2. 2.
    H. Leditschke, Chem. Ber.,86, 123 (1953).Google Scholar

Copyright information

© Consultants Bureau 1971

Authors and Affiliations

  • L. D. Smirnov
    • 1
  • V. I. Kuz'min
    • 1
  • V. P. Lezina
    • 1
  • K. M. Dyumaev
    • 1
  1. 1.Institute of Chemical PhysicsAcademy of Sciences of the USSRUSSR

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