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Synthesis and stereoisomerism of n-oxides of the decahydroquinoline series

Research paper by A. A. Akhrem, L. I. Ukhova, N. F. Marcheako, N. F. Uskova

Indexed on: 01 Dec '68Published on: 01 Dec '68Published in: Russian Chemical Bulletin



Abstract

In the oxidation of 4-ethynyl-, 4-vinyl-, and 4-ethyl-decahydro-1,2-dimethyl-4-quinolinols containing an axial methyl group at C-2 with hydrogen peroxide only one isomer of the N-oxide is formed.In the oxidation of 4-ethynyl-, 4-vinyl-, and 4-ethyl-decahydro-1,2-dimethyl-4-quinolinole containing an equatorial methyl group at C-2 with hydrogen peroxide two isomeric N-oxides are formed.In the oxidation of the isomeric decahydro-1,2-dimethyl-4-vinyl-4-quinolinols with two molecular proportions of peracetic acid the main products are the corresponding 4-(epoxyethyl)decahydro-1,2-dimethyl-4-quinolinol 1-oxides.