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 Full article
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Russian Journal of Organic Chemistry
ISSN: 1070-4280 , E-ISSN: 1608-3393 |
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| Output data | Year: 2011, Volume: 47, Number: 4, Pages: 581-588 Pages count : DOI: 10.1134/S1070428011040191 | ||
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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 OpenAlex
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 OpenAlex
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
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 |