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

ArticleLinkType.TRANSLATED_TO_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

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

Altmetrics: