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THE STRUCTURE OF PRODUCTS OF PHENACYLATION AND SUBSEQUENT (RE)CYCLIZATIONS OF 3-ACETYL-4,6-DIMETHYLPYRIDIN-2(1H)-ONE ACCORDING TO X-RAY STRUCTURAL ANALYSIS

Екатерина M. Окуль, Виктор Б. Рыбаков, Евгений В. Бабаев
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Abstract


A novel phenacylation reaction of an acetylpyridone has been described for the first time, where isomeric O- and N-substitution products were formed which then underwent cyclization under basic conditions with the formation of furo[2,3-b]pyridine and indolizin-5-one. Cyclization of the N-isomer under acidic conditions lead to an [1,3]oxazolo[3,2-a]pyridin-1-ium salt, which transformed into 5-morpholinoindolizine by the action of morpholine, and into oxazolylpyridine by the action of ammonia. Structures of the products were established by X-ray structural analysis.

Authors: Ekaterina M. Okul', Victor B. Rybakov, Eugene V. Babaev*


Keywords


furan; indolizine; oxazole; pyridine; pyridone; pyrrole; cyclization; phenacylation; recyclization

Full Text: PDF (Russian) Supplementary File(s): Supporting information (321KB)


 

 

Latvian Institute of Organic Synthesis - Aizkraukles iela, 21, Riga, LV-1006, Latvia - hgs@osi.lv