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

Authors

  • В. А. Мамедов A. E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center, Russian Academy of Sciences
  • А. Т. Губайдуллин A. E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center, Russian Academy of Sciences
  • Е. А. Хафизова A. E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center, Russian Academy of Sciences
  • А. И. Самигуллина A. E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center, Russian Academy of Sciences
  • И. Бауер Institute of Organic Chemistry, Dresden University of Technology
  • В. Д. Хабихер Institute of Organic Chemistry, Dresden University of Technology

DOI:

https://doi.org/10.1007/1473

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

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

Author Biographies

В. А. Мамедов, A. E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center, Russian Academy of Sciences

Вахид Абдулла-оглы Мамедов

заведующий лабораторией Химии гетеро­цик­лических соединений УРАН ИОФХ им. А.Е. Арбузова КазНЦ РАН д.х.н., профессор

А. Т. Губайдуллин, A. E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center, Russian Academy of Sciences

Айдар Тимургалеевич Губайдуллин

Е. А. Хафизова, A. E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center, Russian Academy of Sciences

Елена Анатольевна Хафизова

А. И. Самигуллина, A. E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center, Russian Academy of Sciences

Аида Ильдусовна Самигуллина

И. Бауер, Institute of Organic Chemistry, Dresden University of Technology

Ингмар Бауер

В. Д. Хабихер, Institute of Organic Chemistry, Dresden University of Technology

Вольф Дитер Хабихер

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Published

2014-02-28

Issue

No. 2 (2014)

Section

Original Papers