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Reaction of N ‐amino‐4,6‐dimethylpyrimidinium mesitylene sulfonate with nucleophiles . A 15 n‐study
Author(s) -
van der Plas Henk C.,
Baloniak Sylwester,
Jongejan Hugo
Publication year - 1983
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570200227
Subject(s) - chemistry , mesitylene , nucleophile , hydrazine (antidepressant) , sulfonate , sodium hydroxide , medicinal chemistry , base (topology) , amide , aqueous solution , ammonia , organic chemistry , hydrate , salt (chemistry) , polymer chemistry , sodium , toluene , catalysis , mathematical analysis , mathematics , chromatography
Reaction of N ‐amino‐4, 6‐dimethylpyrimidinium mesitylene sulfonate with liquid ammonia, with an aqueous solution of sodium hydroxide or with hydrazine leads to 3, 5‐dimethylpyrazole. Reaction of this salt with 15 N ‐labelled hydrazine gave incorporation of nitrogen‐15 in 3,5‐dimethylpyrazole and in recovered starting material. Evidence has been presented that the initial step in the ring contraction with hydrazine is the addition of the nucleophile to C‐2 and C‐6. It is suggested that in the presence of a base the reactive species is probably 4,6‐dimethylpyrimidinio amide.