Reduction of Nitroso Group in Heterocyclics


IN search of a better and convenient method for the reduction of the 5-nitroso group of substituted pyrimidines, an intermediate for the synthesis of substituted pteridines, required for the synthesis of antagonist of folic acid, as a possible tumour-inhibiting agent (cf. aminopterin and amethopterin), nickel–aluminium alloy in alkaline solution is found to be a very suitable and convenient reagent. Besides the use of nickel–aluminium alloy as catalyst for hydrogenation of various unsaturated compounds, it has been used most successfully in alkaline medium for the reduction of carbonyl groups to the corresponding hydrocarbons or carbinols1, for the exchange of halogens by hydrogens2, for the reduction of isolated, conjugated or cyclic double bonds3, for the hydrogenolysis of alkoxy or methylene dioxy groups in aromatic compounds4, various sulphur compounds5 and furan derivatives6.

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KOY, N., KUNDU, N. Reduction of Nitroso Group in Heterocyclics. Nature 188, 581–582 (1960).

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