Abstract
Heating of 2,3-cycloalkenobenzopyrylium salts in acetic anhydride with excess formylating agent (dimethylformamide, formanilide, N-formylmorpholine, and N-phenyl-N-methyl-aminoacrolein) gives monoiminium salts, the hydrolysis of which yields aldehydes or, in the presence of hydrosulfide, thioaldehydes. On treatment with the Vilsmeier complex, 1-methylquinaldinium salts give diiminium salts, which are hydrolyzed to the corresponding aldehydes.
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V. I. Minkin and G. N. Dorofeenko, Usp. Khim., 29, 599 (1960).
Z. Arnold, Zh. Vses. Khim. Obshchestva, 7, 390 (1962).
I. G. Dingwall, D. H. Reid, and K. Wade, J. Chem. Soc., C, 913 (1969).
G. A. Reynolds and I. A. Van Allan, J. Org. Chem., 34, 2736 (1969).
V. L. Zbarskii, G. M. Shutov, V. F. Zhilin, and E. Yu. Orlova, Zh. Organ. Khim., 4, 1970 (1968).
F. M. Hammer, The Cyanine Dyes and Related Compounds, Vol. 4 (1964).
I. Russel and M. Speak, J. Am. Chem. Soc., 63, 851 (1941).
A. Ridgway and I. Robinson, J. Chem. Soc., 214 (1924).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 733–736, June, 1971.
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Shelepin, N.E., Loseva, N.S., Nivorozhkin, L.E. et al. Formylation and vinylformylation of 2,3-cycloalkenobenzopyrylium salts. Chem Heterocycl Compd 7, 684–686 (1971). https://doi.org/10.1007/BF00476806
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DOI: https://doi.org/10.1007/BF00476806