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Adamantylated Calix[4]arenes Bearing CuAAC-Ready 2-Azidoethyl or Propargyl Functionalitiesстатья Исследовательская статья
Дата последнего поиска статьи во внешних источниках: 22 мая 2024 г.
- Авторы: Gorbunov Alexander, Malakhova Maria, Bezzubov Stanislav, Lentin Ivan, Kovalev Vladimir, Vatsouro Ivan
- Журнал: MolBank
- Том: 2024
- Номер: 2
- Год издания: 2024
- Издательство: MDPI
- Местоположение издательства: Basel, Switzerland
- Номер статьи: M1821
- DOI: 10.3390/m1821
- Аннотация: 1,3-Alternate calix[4]arenes were prepared, having bulky adamantyl groups in the p-positions of all four aromatic units of the macrocycles and pairs of propargyl or 2-azidoethyl groups alternating with n-propyl groups at the phenol oxygen atoms. The step-wise syntheses were carried out through a selective distal alkylation of the parent p-adamantylcalix[4]arene with propargyl bromide or 1,2-dibromoethane, resulting in calix[4]arenes bearing pairs of propargyl or 2-bromoethyl groups at their narrow rims. The bromine atoms were replaced by azide groups, and then both calix[4]arene diethers were exhaustively alkylated at the remaining OH-groups with 1-iodopropane under stereoselective conditions to fix the macrocycles in an 1,3-alternate shape. The structures of the prepared p-adamantylcalix[4]arenes were confirmed by NMR and HRMS data, and, for the 1,3-alternate dipropargyl ether, the X-ray diffraction data were also collected. Preliminary data on the reactivity of the prepared calixarenes under the CuAAC conditions suggested a strong steric hampering created by the adamantane units nearby the reacting alkyne or azide groups that affected the outcome of the two-fold cycloaddition involving the calixarene bis(azides) or bis(alkynes) as complementary partners.
- Добавил в систему: Вацуро Иван Михайлович
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