Advertisement

Chemistry of Heterocyclic Compounds

, Volume 29, Issue 3, pp 356–361 | Cite as

Influence of substituents in salicylaldehyde molecule on interaction with 2-imino-3,5-dimethylthiazolidine

  • N. A. Martem'yanova
  • Yu. M. Chunaev
  • N. M. Przhiyalgovskaya
  • L. N. Kurkovskaya
  • O. S. Filipenko
  • S. M. Aldoshin
Article
  • 32 Downloads

Abstract

Salicylaldehyde, 5-chlorosalicylaldehyde, or o-vanillin will react with 2-imino-3,5-dimethylthiazolidine to form previously unknown bis(3,5-dimethylthiazolidin-2-ylideneamino)-2-hydroxyphenylmethanes. If strong electron-acceptor groups are present on the aromatic ring, an acid-base interaction takes place. Thus, 3-nitro-5-methoxy-, 3-nitro-5-chloro-, and 3-bromo-5-nitrosalicylaldehyde react with the heterocyclic base to form saltlike complexes, the structure of which has been confirmed by x-ray diffraction.

Keywords

Organic Chemistry Aromatic Ring Salicylaldehyde Heterocyclic Base Dimethylthiazolidine 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    R. C. Bertelson, “Spiropyrans and related compounds,” in: Photochromism, G. H. Brown (ed.), Wiley, New York (1971), p. 49.Google Scholar
  2. 2.
    Yu. M. Chunaev and N. M. Przhiyalgovskaya, “2-Methyleneindoline bases: synthesis and properties,” Itogi Nauki Tekh. (VINITI, Moscow) (1990), Vol. 14, p. 127.Google Scholar
  3. 3.
    Fuji Photo Film Co., Br. Pat. 1,275,695, Chem. Abstr., 75, 22847 (1971).Google Scholar
  4. 4.
    R. Schapiro, D. G. Doherty, and W. T. Burnett, Radiat. Res., 7, 28 (1957).Google Scholar
  5. 5.
    T. W. Balko to Eli Lilly & Co., Br. Pat. 2,010,828, Chem. Abstr., 92, 163958 (1980).Google Scholar
  6. 6.
    C. S. Rooney, J. Rokach, and E. Gragoe to Merck & Co., FRG Pat. 2,719,577, Chem. Abstr., 88, 62384 (1978).Google Scholar
  7. 7.
    C. Barrie and Ch. Charles, Eur. Pat. 11,963, Chem. Abstr., 94, 103347 (1981).Google Scholar
  8. 8.
    H. M. Bogaert, D. J. Zwanenburg, and Th. A. M. M. Maas, Rec. Trav. Chim., 94, 218 (1975).Google Scholar
  9. 9.
    S. Gabriel, Ber. Dtsch. Chem. Ges., 22, 2984 (1889).Google Scholar
  10. 10.
    G. M. Sheldrick, SHELXS-86: Programme for Crystal Structure Determination, Cambridge University Press (1986).Google Scholar

Copyright information

© Plenum Publishing Corporation 1993

Authors and Affiliations

  • N. A. Martem'yanova
    • 1
    • 2
  • Yu. M. Chunaev
    • 1
    • 2
  • N. M. Przhiyalgovskaya
    • 1
    • 2
  • L. N. Kurkovskaya
    • 1
    • 2
  • O. S. Filipenko
    • 1
    • 2
  • S. M. Aldoshin
    • 1
    • 2
  1. 1.D. I. Mendeleev Moscow Chemical Technology InstituteMoscow
  2. 2.Branch of the Institute of Chemical PhysicsRussian Academy of SciencesChernogolovka

Personalised recommendations