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.
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References
R. C. Bertelson, “Spiropyrans and related compounds,” in: Photochromism, G. H. Brown (ed.), Wiley, New York (1971), p. 49.
Yu. M. Chunaev and N. M. Przhiyalgovskaya, “2-Methyleneindoline bases: synthesis and properties,” Itogi Nauki Tekh. (VINITI, Moscow) (1990), Vol. 14, p. 127.
Fuji Photo Film Co., Br. Pat. 1,275,695, Chem. Abstr., 75, 22847 (1971).
R. Schapiro, D. G. Doherty, and W. T. Burnett, Radiat. Res., 7, 28 (1957).
T. W. Balko to Eli Lilly & Co., Br. Pat. 2,010,828, Chem. Abstr., 92, 163958 (1980).
C. S. Rooney, J. Rokach, and E. Gragoe to Merck & Co., FRG Pat. 2,719,577, Chem. Abstr., 88, 62384 (1978).
C. Barrie and Ch. Charles, Eur. Pat. 11,963, Chem. Abstr., 94, 103347 (1981).
H. M. Bogaert, D. J. Zwanenburg, and Th. A. M. M. Maas, Rec. Trav. Chim., 94, 218 (1975).
S. Gabriel, Ber. Dtsch. Chem. Ges., 22, 2984 (1889).
G. M. Sheldrick, SHELXS-86: Programme for Crystal Structure Determination, Cambridge University Press (1986).
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Deceased.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 420–425, March, 1993.
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Martem'yanova, N.A., Chunaev, Y.M., Przhiyalgovskaya, N.M. et al. Influence of substituents in salicylaldehyde molecule on interaction with 2-imino-3,5-dimethylthiazolidine. Chem Heterocycl Compd 29, 356–361 (1993). https://doi.org/10.1007/BF00531517
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DOI: https://doi.org/10.1007/BF00531517