Pyrimidine reactions. Part XVIII. The conversion of 4-methoxy-5-nitropyrimidine into 3-amino-4-nitropyrazole by hydrazine

doi:10.1039/J39680002159

Paper

Pyrimidine reactions. Part XVIII. The conversion of 4-methoxy-5-nitropyrimidine into 3-amino-4-nitropyrazole by hydrazine

Published 1968 · M. Biffin, D. J. Brown, Q. N. Porter

Journal of The Chemical Society C: Organic

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Abstract

4-Methoxy-5-nitropyrimidine reacts with ethanolic hydrazine hydrate below 0° to give 4-hydrazino-5-nitropyrimidine which is converted by an excess of hydrazine hydrate at 25° into 3-amino-4-nitropyrazole. The mechanism, unprecedented in transformations of pyrimidines into pyrazoles, is discussed.The nitropyrazoles undergo hydrogenation to ortho-diamines which condense with α-dicarbonyl compounds to give pyrazolo[3,4-b]pyrazine and appropriate derivatives. Assigned structures are consistent with the measured u.v., i.r., 1H n.m.r., and mass spectra, and with ionization constants.

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Hydrazine hydrate catalyzes a novel transformation of 4-methoxy-5-nitropyrimidine into 3-amino-4-nitropyrazole, a novel mechanism in pyrimidine reactions.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Pyrimidine reactions. Part XVIII. The conversion of 4-methoxy-5-nitropyrimidine into 3-amino-4-nitropyrazole by hydrazine

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References

Citations

Reaction of 6-methyl-2-(2-oxo-2-phenyl-ethylidene)-2,3-dihydropyrimidin-4(1H)-one with hydrazine and hydroxylamine

The reaction of 6-methyl-2-(2-oxo-2-phenylethylidene)-2,3-dihydropyrimidin-4(1H)-one with hydrazine yields 3-amino-5-phenylpyrazole and 3-methyl-2-pyrazolin

Ring transformations in reactions of heterocyclic compounds with nucleophiles (III): Conversion of pyrimidine and some of its methyl derivatives by hydrazine and by methylhydrazine sulfate into pyrazoles and methylpyrazoles

Pyimidine and its methyl derivatives can be converted into pyrazoles and methylpyrazoles by hydrazine and methylhydrazine sulfate, with a proposed mechanism involving an open-chain intermediate.

Conversion of 4,6‐disubstituted pyrimidines into 1,2,4‐Triazoles by action of Hydrazine

Hydrazine can convert 4,6-disubstituted pyrimidines into 1,2,4-triazoles, involving the C(2)-N(3 or 1)-C(4 or 6)-C(5) fragment of the pyrimidine ring.

Ring transformations in reactions of heterocyclic compounds with nucleophiles (XV) Reactions of N-aminopyrimidinium salts with liquid ammonia†‡

N-aminopyrimidinium salts show diverse reactions with liquid ammonia, resulting in proton abstraction, adduct formation, and deamination, with ring opening/ring closure sequences being proven.

Ring transformations in reactions of heterocyclic compounds with nucleophiles (X). A novel pyrimidine rearrangement reaction

This novel pyrimidine rearrangement reaction involves the attack of the nucleophilic end of the side-chain at position 5 on C(6) and simultaneous fission of the N(1)-C(6) bond.