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TRANSFORMATIONS OF SUBSTITUTED OXAZOLO[3,2-a]PYRIDINES TO 5,6-DISUBSTITUTED INDOLIZINES: SYNTHESIS AND X-RAY STRUCTURAL MAPPING

В. Б. Рыбаков, Е. В. Бабаев
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Abstract


The treatment of 4,6-dimethyl-2-oxonicotinic nitrile, amide, and ethyl ester with p-bromophenacyl bromide produced N-alkyl isomers, which cyclized in the presence of mineral acids to the oxazolo[3,2‑a]pyridinium cations without changes in the functional groups. The obtained compounds underwent recyclization to 6-Х-5-aminoindolizines (X = CN, CONH2, CO2Et) upon treatment with morpholine. The compounds were characterized by X-ray structural analysis.

How to Cite
Rybakov, V. B.; Babaev, E. V. Chem. Heterocycl. Compd. 2014, 50, 225. [Khim. Geterotsikl. Soedin. 2014, 250.]

For this article in the English edition see DOI 10.1007/s10593-014-1465-8


Keywords


4,6 dimethyl-2 oxonicotinic acid derivatives; indolizines; oxazolo[3,2-a]pyridinium salts; phenacylation; rearrangement

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