Abstract
Condensation of cinchomeronic acid with p-nitrophenylacetic acid, of 2, 6-dimethylcinchomeronic acid with phenylacetic acid, and p-nitrophenylacetic acid in acetic anhydride solution in the presence of triethylamine followed by rearrangement of the condensation products with sodium methoxide gives 2-(p-nitrophenyl)-5-azaindandione-1, 3, 4, 6-dimethyl-2-phenyl-5-azaindandione-1, 3, and 4, 6-dimethyl-2-(p-nitrophenyl)-5-azaindandione-1, 3. Reaction of the alkali metal salts of these compounds with dimethyl sulfate leads to alkylation at the nitrogen atom, and formation of N-methyl betaines of the corresponding 5-azaindandiones. 2-Aryl-5-azaindandiones and their N-methyl betaines are dark in color (black to reddish brown), sparingly soluble, and decompose at 250-350°.
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References
L. E. Neiland and G. Ya. Vanag, Izv. AN Latv. SSR, Ser. khim., 203, 1964.
L. E. Neiland and G. Ya. Vanag, KhGS [Chemistry of Heterocyclic Compounds], 93, 1965.
L. E. Neiland and G. Ya. Vanag, KhGS [Chemistry of Heterocyclic Compounds], 884, 1965.
L. E. Neiland and V. Kroge, AN Latv. SSR, ser. khim., 483, 1964.
A. K. Aren, O. Ya. Neiland, and G. Ya. Vanag, DAN, 132, 115, 1960.
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Neiland, L.E., Vanag, G.Y. Some 2-aryl-5-azaindandiones-1, 3. Chem Heterocycl Compd 1, 597–599 (1966). https://doi.org/10.1007/BF00472699
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DOI: https://doi.org/10.1007/BF00472699