On the reactivity of  N ‐benzylpyrimidinium salts with nitrogen nucleophiles | Zendy

Dlugosz A. | Zendy; van der Plas H. C. | Zendy; Van Veldhuizen A. | Zendy

AI Assistant Blog Pricing

Home ZAIA Blog

Premium

On the reactivity of N ‐benzylpyrimidinium salts with nitrogen nucleophiles

Author(s) -

Dlugosz A.,

van der Plas H. C.,

Van Veldhuizen A.

Publication year - 1982

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.5570190231

Subject(s) - chemistry , hydrazine (antidepressant) , bromide , nucleophile , reactivity (psychology) , ammonia , medicinal chemistry , liquid ammonia , nitrogen , benzyl bromide , organic chemistry , labelling , pyrimidine , stereochemistry , catalysis , medicine , biochemistry , alternative medicine , chromatography , pathology

Treatment of the l‐benzyl salts of pyrimidine, 4,6‐dimethylpyrimidine, and 4‐ t ‐butylpyrimidine with liquid ammonia leads to debenzylation. The 1 H‐nmr spectroscopic evidence is presented that the initial step in the debenzylation of l‐benzyl‐4,6‐dimethylpyrimidinium bromide is the addition of the ammonia at C‐2, while with l‐benzyl‐4‐ t ‐butylpyrimidinium bromide the addition takes place at C‐6. It is proved by 15 N labelling that the debenzylation occurs according to the ANRORC mechanism. The above‐mentioned l‐benzylpyrimidinium bromides give with hydrazine, pyrazole, 3,5‐dimethylpyrazole and 3‐ t ‐butylpyrazole, respectively.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research