Meta/meta- and meta/para-disubstituted organomercury calix[4]arenes in the cone conformation were transformed into corresponding amino derivatives. Acylation and subsequent intramolecular cyclization using the Bischler-Napieralski reaction provided, in the case of the meta/meta-series, double bridged calixarenes possessing seven membered rings on the upper rim. A similar synthetic strategy applied to meta/para-isomers allowed for the isolation of monobridged compounds bearing an additional trifluoroacetamido group located distally to seven-membered rings. Both series represent inherently chiral systems, which were successfully resolved using preparative chiral HPLC. The pure enantiomers exhibited a recognition ability towards selected chiral guest molecules as documented by the 1H NMR titration experiments. The absolute configuration of the phenyl-substituted enantiomer (meta/meta-) was confirmed by single crystal structure determination (X-ray).

Department of Organic Chemistry University of Chemistry and Technology Prague Technická 5 166 28 Prague 6 Czech Republic

Department of Solid State Chemistry UCTP Technická 5 166 28 Prague 6 Czech Republic

Institute of Physics AS CR v v i Na Slovance 2 182 21 Prague 8 Czech Republic

Zobrazit více v PubMed

Neri P., Sessler J. L. and Wang M. X., Calixarenes and Beyond, Springer, Cham, Switzerland, 2016

Gutsche C. D., Calixarenes: An Introduction, Royal Society of Chemistry, Cambridge, U.K., 2nd edn, 2008

Vicens J., Harrowfield J. and Backlouti L., Calixarenes in the Nanoworld, Springer, Dordrecht, The Netherlands, 2007

Asfari Z., Böhmer V., Harrowfield J. and Vicens J., Calixarenes 2001, Kluwer, Dordrecht, The Netherlands, 2001

Mandolini L. and Ungaro R., Calixarenes in Action, Imperial College Press, London, 2000

Kelderman E. Verboom W. Engbersen J. F. J. Reinhoudt D. N. Heesink G. J. T. van Hulst N. F. Derhaeg L. Persoons A. Angew. Chem., Int. Ed. Engl. 1992;31:1075–1077. doi: 10.1002/anie.199210751. DOI

Shinkai S. Araki K. Tsubaki T. Arimura T. Manabe O. J. Chem. Soc., Perkin Trans. 1. 1987:2297–2299. doi: 10.1039/P19870002297. DOI

Gutsche C. D. Pagoria P. F. J. Org. Chem. 1985;50:5795–5802. doi: 10.1021/jo00350a071. DOI

Slavik P. Dudic M. Flidrova K. Sykora J. Cisarova I. Böhm S. Lhotak P. Org. Lett. 2012;14:3628–3631. doi: 10.1021/ol301420t. PubMed DOI

Flídrová K. Slavík P. Eigner V. Dvořáková H. Lhoták P. Chem. Commun. 2013;49:6749–6751. doi: 10.1039/C3CC43284J. PubMed DOI

Slavík P. Eigner V. Lhoták P. Org. Lett. 2015;17:2788–2791. doi: 10.1021/acs.orglett.5b01200. PubMed DOI

Tlustý M. Slavík P. Kohout M. Eigner V. Lhoták P. Org. Lett. 2017;19:2933–2936. doi: 10.1021/acs.orglett.7b01170. PubMed DOI

Flídrová K. Böhm S. Dvořáková H. Eigner V. Lhoták P. Org. Lett. 2014;16:138–141. doi: 10.1021/ol403133b. PubMed DOI

Slavík P. Eigner V. Lhoták P. CrystEngComm. 2016;18:4964–4970. doi: 10.1039/C6CE00314A. DOI

Vrzal L. Flídrová K. Tobrman T. Dvořáková H. Lhoták P. Chem. Commun. 2014;50:7590–7592. doi: 10.1039/C4CC02274B. PubMed DOI

Movassaghi M. Hill M. D. Org. Lett. 2008;10:3485–3488. doi: 10.1021/ol801264u. PubMed DOI PMC

Arnott G. E. Chem.–Eur. J. 2018;24:1744–1754. doi: 10.1002/chem.201703367. PubMed DOI

Neri P., Sessler J. L. and Wang M. X., Calixarenes and Beyond, Springer, Cham, Switzerland, 2016

Li S. Y. Xu Y. W. Liu J. M. Su C. Y. Int. J. Mol. Sci. 2011;12:429–455. doi: 10.3390/ijms12010429. PubMed DOI PMC

Szumna A. Chem. Soc. Rev. 2010;39:4274–4285. doi: 10.1039/B919527K. PubMed DOI

The binding constants were calculated using the Bindfit application freely available at: http://supramolecular.org

Hibbert D. B. Thordarson P. Chem. Commun. 2016;52:12792–12805. doi: 10.1039/C6CC03888C. PubMed DOI

Ulatowski F. Dabrowa K. Balakier T. Jurczak J. J. Org. Chem. 2016;81:1746–1756. doi: 10.1021/acs.joc.5b02909. PubMed DOI

Thordarson P. Chem. Soc. Rev. 2011;40:1305–1323. doi: 10.1039/C0CS00062K. PubMed DOI

Palatinus L. Chapuis G. J. Appl. Crystallogr. 2007;40:786–790. doi: 10.1107/S0021889807029238. DOI

Altomare A. Cascarano G. Giacovazzo C. Guagliardi A. Burla M. C. Polidori G. Camalli M. J. Appl. Crystallogr. 1994;27:435–436.

Betteridge P. W. Carruthers J. R. Cooper R. I. Prout K. Watkin D. J. J. Appl. Crystallogr. 2003;36:1487. doi: 10.1107/S0021889803021800. DOI

Lusi M. CrystEngComm. 2018;20:7042–7052. doi: 10.1039/C8CE00691A. DOI

Rohlicek J. Husak M. J. Appl. Crystallogr. 2007;40:600–601. doi: 10.1107/S0021889807018894. DOI

Upper rim-bridged calixarenes

The Formation of Inherently Chiral Calix[4]quinolines by Doebner-Miller Reaction of Aldehydes and Aminocalixarenes