| Autor: |
Liu SN; State Key Laboratory of Applied Organic Chemistry and College of Chemistry & Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China., Ren QX; State Key Laboratory of Applied Organic Chemistry and College of Chemistry & Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China., Ding YT; State Key Laboratory of Applied Organic Chemistry and College of Chemistry & Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China., Cao XP; State Key Laboratory of Applied Organic Chemistry and College of Chemistry & Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China., Shi ZF; State Key Laboratory of Applied Organic Chemistry and College of Chemistry & Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China., Chow HF; Department of Chemistry, The Chinese University of Hong Kong, Shatin, NT 999077, Hong Kong., Kuck D; Department of Chemistry and Center for Molecular Materials (CM2), Bielefeld University, 33615 Bielefeld, Germany. |
| Abstrakt: |
The hitherto unknown hexakis(halomethyl)-functionalized tribenzotriquinacenes (TBTQs) 9 and 10 were synthesized from the key 4b,8b,12b-tribromo-TBTQ derivative 6 by an improved route in 67% overall yield. Extension of the bowl-shaped framework of 9 or 10 by threefold condensation with propargylamine or 2-azidoethylamine afforded the corresponding TBTQ-trialkyne 11 and TBTQ-triazide 12 , respectively. While attempts to construct bis-TBTQ cages, including homodimerization of 11 and heterocoupling of 11 with 12 , were unsuccessful, triazide 12 was found to undergo threefold [3 + 2]-cycloaddition with 3-ethynylaniline and phloroglucinol tripropargyl ether under click chemistry conditions. The latter reaction enabled facile capping of the TBTQ bowl to give the novel cage compound 5 in 22% yield. |
