Abstract: Methyl 2-acetylamino-5-[2-(6-methylpyridin-3-yl)vinyl]benzoate reacted with phenacyl bromide to produce quaternary 1-(2-aryl-2-oxoethyl)-2-methyl-5-(4-acetylamino-3-methoxycarbonyl)pyridinium bromides. 1,3-Dipolar cycloaddition of the latter to methyl propynoate and dimethyl but-2-ynedioate gave the corresponding indolizine derivatives containing an anthranilic acid ester moiety. Reactions of acetylenes with N-phenacylpyridinium salts obtained from a diterpene alkaloid derivative, 2-(pyridin-3-yl)vinyl-substituted lappaconitine afforded analogous compounds in which the indolizine fragment is conjugated to the aromatic ring of the alkaloid. 1,3-Dipolar cycloaddition of 1-(2-aryl-2-oxoethyl)-2-methyl-5-(4-acetylamino-3-methoxycarbonyl) pyridinium bromides with methyl propynoate was regioselective.

Cite: Romanov V.E. , Shul'ts E.E. , Shakirov M.M. , Tolstikov G.A.
Alkaloids of Siberia and Altai flora: XVIII. Alkyl 2-acetylamino-5-[2-(pyridin-3-yl)vinyl]benzoates in the synthesis of indolizines containing an anthranilic acid ester moiety
Russian Journal of Organic Chemistry. 2011. V.47. N4. P.581-588. DOI: 10.1134/S1070428011040191 WOS Scopus РИНЦ

ArticleLinkType.TRANSLATED_TO_ORIGINAL: Романов В.Е. , Шульц Э.Э. , Шакиров М.М. , Толстиков Г.А.
Исследование алкалоидов флоры сибири и алтая. xviii. алкил 2-ацетиламино-5-[2-(пиридин-3-ил)винил]бензоаты в синтезе индолизинов антранилатного типа
Журнал органической химии (RUSS J ORG CHEM+). 2011. Т.47. №4. С.578-585. РИНЦ

Dates:

Published print:	Apr 1, 2011
Published online:	May 12, 2011

Identifiers:

Web of science	WOS:000290541100019
Scopus	2-s2.0-79957869251
Elibrary	17001875
OpenAlex	W1975220505

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