1,10-Phenanthroline Carboxylic Acids for Preparation of Functionalized Metal-Organic Frameworks

Abel, A.S.; Mitrofanov, A.Y.; Yakushev, A.A.; Zenkov, I.S.; Morozkov, G.V.; Averin, A.D.; Beletskaya, I.P.; Michalak, J.; Brandès, S.; Bessmertnykh-Lemeune, A.

Авторы: Abel Anton S., Mitrofanov A.Yu, Yakushev Aleksei A., Zenkov Ilya S., Morozkov Gleb V., Averin Alexei D., Beletskaya Irina P., Michalak Julien, Brandès Stéphane, Bessmertnykh-Lemeune Alla
Журнал: Asian Journal of Organic Chemistry
Том: 8
Номер: 11
Год издания: 2019
Первая страница: 2128
Последняя страница: 2142
DOI: 10.1002/ajoc.201900569
Аннотация: Abstract Synthetic approaches to 1,10-phenanthroline-3-carboxylic acid (2), 1,10-phenanthroline-3,8-dicarboxylic acid (3) and their functionalized derivatives were investigated. Acids 2 and 3 were prepared in good yields from bromophenanthrolines via palladium-catalyzed alkoxycarbonylation. Moreover, butyl 8-bromo-1,10-phenanthroline-3-carboxylate was obtained in acceptable yield (25–35%) by ceasing the carbonylation of the dibromide 5 after 30–70% consumption of the starting compound. To prepare functionalized derivatives of acids 2 and 3, the reactions of butyl 8-bromo-1,10-phenanthroline-3-carboxylate and diethyl 4,7-dichloro-1,10-phenanthroline-3,8-dicarboxylate with various nucleophiles were investigated. SNAr reactions are suitable for the synthesis of 4,7-diazido-, dimethoxy- and diamino-substituted 3,8-bis(ethoxycarbonyl)phenanthrolines, including the macrocyclic derivatives. The bromine atom at position 8 of the phenanthroline ring reacts with nucleophiles only in the presence of the palladium catalysts. The scope of these reactions was briefly investigated conducting Sonogashira, Suzuki-Miyaura and Hirao reactions. Hydrolysis of the functionalized esters of phenanthroline leads to corresponding acids in good yields.
Добавил в систему: Абель Антон Сергеевич

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1,10-Phenanthroline Carboxylic Acids for Preparation of Functionalized Metal-Organic Frameworksстатья

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