Heterocyclic studies. Part VII. Action of methoxyamine and methylhydrazines on 4-hydroxypteridine and its methyl derivatives

doi:10.1039/J39690001297

Paper

Heterocyclic studies. Part VII. Action of methoxyamine and methylhydrazines on 4-hydroxypteridine and its methyl derivatives

Published 1969 · Jim D. Clark, G. Neath, Carroll N. Smith

Journal of The Chemical Society C: Organic

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2

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0

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Abstract

Unsymmetrical dimethylhydrazine reacted with 4-hydroxypteridine and its 2-methyl derivative to give mixtures of an aminopyrazine carboxamide (III; R2= R3= H), an aminopyrazine carbohyrazide (IVb; R2= R3= H), and 4,5-diamino-6-hydroxypyrimidine (IX; R1= H or Me). The 6- and 7-methyl and 6,7- and 2,7-dimethyl derivatives of 4-hydroxypteridine gave analogous products except that no pyrimidine derivative was obtained in these cases. Methylhydrazine degraded 4-hydroxypteridines similarly.4-Hydroxypteridine and its 2- and 6-methyl derivatives were cleaved by methoxyamine to yield 4,5-diamino-6-hydroxypyrimidines (IX; R1= H or Me) and in two cases pyrazine derivatives (VIc; R2= H or Me, R1= R3= H) which still contained all the carbon atoms of the original pteridines. 4-Hydroxy-7-methylpteridine and methoxyamine gave only the pyrazine derivative (Vlc; R1= R2= H, R3= Me) while 2,7- and 6,7-dimethyl-4-hydroxypteridine gave methyl aminopyrazine carbohydroxamates (IVc; R2= H or Me, R3= Me) under the more vigorous conditions necessary for their cleavage. 1 H N.m.r. data for the products are recorded and possible mechanisms for pyrazine ring cleavage are suggested.

Study Snapshot

Methoxyamine and methylhydrazines can degrade 4-hydroxypteridine and its methyl derivatives to yield 4,5-diamino-6-hydroxypyrimidines and pyrazine derivatives, respectively.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Heterocyclic studies. Part VII. Action of methoxyamine and methylhydrazines on 4-hydroxypteridine and its methyl derivatives

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References

Citations

Derivatives of 3-Aminopyrazine-2-carboxamides: Synthesis, Antimicrobial Evaluation, and in Vitro Cytotoxicity

The series of N-substituted 3-aminopyrazine-2-carboxamides show antimicrobial activity against various bacteria, fungi, and viruses, with compound 20 showing some cytotoxicity in HepG2 cancer cells.

Recent Advances in Pyazine Chemistry

Recent advances in pyazine chemistry include the development of new synthetic pyrazines with diverse physiological activities, potential as bidentate ligands, and aromatic properties.