Reduction of Nitroso Group in Heterocyclics

Abstract

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.

Access options

Rent or Buy article

Get time limited or full article access on ReadCube.

from$8.99

All prices are NET prices.

References

  1. 1

    Papa, D., Schwenk, E., and Whitman, B., J. Org. Chem., 7, 587 (1942).

  2. 2

    Schwenk, E., Papa, D., Whitman, B., and Ginsberg, H., J. Org. Chem., 9, 1 (1944).

  3. 3

    Schwenk, E., and Papa, D., J. Org. Chem., 9, 175 (1944).

  4. 4

    Schwenk, E., and Papa, D., J. Org. Chem., 10, 232 (1945).

  5. 5

    Papa, D., Schwenk, E., and Ginsberg, H. F., J. Org. Chem., 14, 723 (1949).

  6. 6

    Papa, D., Schwenk, E., and Ginsberg, H. F., J. Org. Chem., 16, 253 (1951).

  7. 7

    Cain, C. K., Mallette, M. F., and Taylor, jun., E. C., J. Amer. Chem. Soc., 68, 1998 (1946).

  8. 8

    Baker, B. R., Joseph, J. P., and Schaub, R. E., J. Org. Chem., 19, 631 (1954).

  9. 9

    Cason, J., in “Organic Synthesis”, 37, 15 (1957).

Download references

Author information

Affiliations

Authors

Rights and permissions

Reprints and Permissions

About this article

Cite this article

KOY, N., KUNDU, N. Reduction of Nitroso Group in Heterocyclics. Nature 188, 581–582 (1960). https://doi.org/10.1038/188581a0

Download citation

Comments

By submitting a comment you agree to abide by our Terms and Community Guidelines. If you find something abusive or that does not comply with our terms or guidelines please flag it as inappropriate.