Alkaloids of the flora of Siberia and Altai: XX. Synthesis of 5-aryl(hetaryl)-substituted anthranilic acid esters 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: 2014, Volume: 50, Number: 7, Pages: 960-972 Pages count : 13 DOI: 10.1134/S1070428014070070 | ||||
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Abstract:
Cross-coupling of methyl 2-acetylamino-5-bromobenzoate and 5'-bromolappaconitine with aryl-, furyl-, pyridyl-, and 5-acetylthiophen-2-ylboronic acids or 1-(2-fluoroquinolin-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane gave the corresponding 5-aryl(hetaryl)-substituted anthranilic acid derivatives. The use of the two-phase toluene-water system as reaction medium and addition of tetrabutylammonium bromide allows the cross-coupling to be accomplished under mild conditions. The catalytic system Pd(dba)(2)-AsPh3 was found to be efficient in the cross-coupling of methyl 2-acetylamino-5-bromobenzoate with furyl- and pyridylboronic acids, whereas the system Pd(OAc)(2)-(o-Tol)(3)P ensured good results in the reactions of 5'-bromolappaconitine with hetarylboronic acids. Facile esterification at the C-8-OH and C-9-OH groups of the aconitane skeleton was observed in the reactions of 5'-bromolappaconitine and 5'-phenyllappaconitine with phenylboronic acid. 5'-Bromo-8,9-O-(phenylboranediyl)lappaconitine under the Suzuki reaction conditions underwent hydrolysis of the boronic ester moiety with formation of the cross-coupling product of 5'-bromolappaconitine with phenylboronic acid.
Cite:
Romanov V.E.
, Sabankulova G.R.
, Shakirov M.M.
, Shul'ts E.E.
Alkaloids of the flora of Siberia and Altai: XX. Synthesis of 5-aryl(hetaryl)-substituted anthranilic acid esters
Russian Journal of Organic Chemistry. 2014. V.50. N7. P.960-972. DOI: 10.1134/S1070428014070070 WOS Scopus РИНЦ OpenAlex
Alkaloids of the flora of Siberia and Altai: XX. Synthesis of 5-aryl(hetaryl)-substituted anthranilic acid esters
Russian Journal of Organic Chemistry. 2014. V.50. N7. P.960-972. DOI: 10.1134/S1070428014070070 WOS Scopus РИНЦ OpenAlex
Original:
Романов В.Е.
, Сабанкулова Г.Р.
, Шакиров М.М.
, Шульц Э.Э.
Исследование алкалоидов флоры сибири и алтая. xx. синтез 5-арил(гетарил)замещенных антранилатов
Журнал органической химии (RUSS J ORG CHEM+). 2014. Т.50. №7. С.979-990. РИНЦ
Исследование алкалоидов флоры сибири и алтая. xx. синтез 5-арил(гетарил)замещенных антранилатов
Журнал органической химии (RUSS J ORG CHEM+). 2014. Т.50. №7. С.979-990. РИНЦ
Dates:
| Published print: | Jul 1, 2014 |
| Published online: | Aug 13, 2014 |
Identifiers:
| Web of science: | WOS:000340568100007 |
| Scopus: | 2-s2.0-84940283221 |
| Elibrary: | 24954729 |
| OpenAlex: | W2103661604 |