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Macrocycles Containing Nitrogen Heterocycles 11*. Calixarene Type Macrocycles Based on m-bis(imidazo[1,5-а]quinoxalin-4(5H)-on-1-yl)benzene for the Encapsulation of Organic Guest Molecules

Research paper by V. A. Mamedov, A. T. Gubaidullin, E. A. Khafizova, A. I. Samigullina, I. Bauer, W. D. Habicher

Indexed on: 23 Apr '14Published on: 23 Apr '14Published in: Chemistry of Heterocyclic Compounds



Abstract

The interaction of m-bis(3-phenylimidazo[1,5-a]quinoxalin-4(5Н)-on-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.