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Imidazoles I. N-Alkylation of 4(5)-Nitroimidazoles

Z. Crnić ; PLIVA, Pharmaceutical, Chemical, Food and Cosmetic Industry, Research Institute, I. L. Ribara 89, 41000 Zagreb, Yugoslavia
B. Glunčić ; PLIVA, Pharmaceutical, Chemical, Food and Cosmetic Industry, Research Institute, I. L. Ribara 89, 41000 Zagreb, Yugoslavia

Sažetak

N-Alkylation of 4(5)-nitroimidazoles la-d with 2-chloroethylacetamide
in acetic acid was studied. Time dependent amounts
of the starting compounds 1, as well as of the two series of isomeric
products 2a-d and 3a-d were monitored by preparative chromatography.
While 5-nitro isomers 2 regularly accumulated faster in
the reaction mixture, maximum concentrations were highest during
the first 3-5 hrs, and then remained constant or slowly decreased.
The amounts of 4-nitro isomers 3 increased steadily during the
whole monitoring period (24 hrs). In the absence of alkylating
agent no isomerization of the bases 2 .= 3 was observed. Since both
the bases and conjugate acids of 2a-d reacted with the second mole
of the alkylating agents to produce 3a-d at a much higher rate
then la-d, it is suggested that 3a-d were formed via intermediary
1,3-dialkyl quaternary salts 4a-d. The same isomerization was
observed during the pyrolyses of the hydrochlorides of 2a-d, while
3a-d isomerized affording only traces of 2a-d.

Ključne riječi

Hrčak ID:

194339

URI

https://hrcak.srce.hr/194339

Datum izdavanja:

20.7.1981.

Posjeta: 547 *