Abstract
The condensation of 3,4-dihydronaphthalen-1(2H)-one with methylamine and formaldehyde in acid medium gave N,N-bis(1-oxo-1,2,3,4-tetrahydronaphthalen-2-ylmethyl)methanamine hydrochloride which was converted into 3-methyl-3,3′,4,4′,5,6-hexahydro-1′H,2H-spiro[benzo[f]isoquinoline-1,2′-naphthalen]-1′-one by heating in 48% aqueous HBr or 50% H2SO4. Oxidation of the spiro compound with KMnO4 initially involved the methylene group of the allylamine fragment with formation of the corresponding lactam which then underwent cis-dihydroxylation at C4a and C10b. Oxidation of the same compound with KMnO4 in the presence of some CH acids (trifluoroacetone and 4-bromoacetophenone) or aromatic amines (4-fluoroaniline and 2-bromo-4-nitroaniline) afforded, respectively, 4-acylmethylidene or 4-arylimino derivatives via C-C or C-N cross-coupling at the 4-position.
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Original Russian Text © A.V. Malkova, V.E. Kotsyuba, A.T. Soldatenkov, S.A. Soldatova, K.B. Polyanskii, N.M. Kolyadina, V.N. Khrustalev, 2014, published in Zhurnal Organicheskoi Khimii, 2014, Vol. 50, No. 12, pp. 1816–1822.
For communication XII, see [1].
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Malkova, A.V., Kotsyuba, V.E., Soldatenkov, A.T. et al. Oxidation reactions of azines: XIII. Synthesis, molecular structure, and oxidation reactions of 3-methyl-3,3′,4,4′,5,6-hexahydro-1′H,2H-spiro[benzo[f]isoquinoline-1,2′-naphthalen]-1′-one. Russ J Org Chem 50, 1797–1803 (2014). https://doi.org/10.1134/S1070428014120148
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DOI: https://doi.org/10.1134/S1070428014120148