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MACROCYCLES CONTAINING NITROGEN HETEROCYCLES. 11. CALIXARENE TYPE MACROCYCLES BASED ON m-BIS(IMIDAZO[1,5-а]QUINOXALIN-4(5Н)-ON-1-YL)BENZENE FOR THE ENCAPSULATION OF ORGANIC GUEST MOLECULES

В. А. Мамедов, А. Т. Губайдуллин, Е. А. Хафизова, А. И. Самигуллина, И. Бауер, В. Д. Хабихер
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Abstract


The interaction of m-bis(3-phenylimidazo[1,5-a]quinoxalin-4(5Н)-one-1-yl)benzene and 3,3'-dibromo-methyl-4-methoxybenzophenone in DMSO or DMF in the presence of t-BuOK or K2CO3, respectively, led to the formation of heterocyclophanes as a result of N,N'-alkylation according to the schemes [1+1] and [2+2] in up to 86% total yield, and the main product from [1+1] N,N'-alkylation was formed in a 57% yield. It was established by X-ray structural analysis that the crystal structure of this product consisted of two independent diastereomeric molecules, and their macroheterocyclic cores were described by an enantiomeric relationship with the accuracy down to the position of the methoxy group in the phenyl fragment.

How to Cite
Mamedov, V. A.; Gubaidullin, A. T.; Khafizova, E. A.; Samigullina, A. I.; Bauer, I.; Habicher, W. D. Chem. Heterocycl. Compd. 2014, 50, 237. [Khim. Geterotsikl. Soedin. 2014, 262.]

For this article in the English edition see DOI 10.1007/s10593-014-1466-7


Keywords


m-bis(3-phenylimidazo[1,5-a]quinoxalin-4(5Н)-one-1-yl)benzene; 3,3'-dibromomethyl-4 methoxybenzophenone; alkylation; encapsulation; macrocyclization; X-ray structural analysis; NMR spectroscopy

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