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Synthesis 2022; 54(05): 1301-1308
DOI: 10.1055/a-1668-9694
DOI: 10.1055/a-1668-9694
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Azide Decomposition as a Pathway to Intramolecularly Upper-Rim-Bridged Calix[4]arenes
This research was supported by the Grantová Agentura České Republiky (Czech Science Foundation; Grant No. 20-07833S). Financial support from Ministerstvo Školství, Mládeže a Tělovýchovy (Ministry of Education, Youth and Sport of the Czech Republic; Grant Nos. A2 FCHT 2021 021 and A1 FCHT 2021 008) is also acknowledged.
Abstract
Proximally single-atom-bridged calix[4]arenes possess a rigidified cavity and, thus, unusual complexation properties. Here, we report on the synthesis of the first such heteroatom-bridged compound: amine-bridged calix[4]arene. This compound, prepared by thermal decomposition of 4-azidocalix[4]arene, was obtained alongside very interesting rearranged, inherently chiral 10H-azepino[1,2-a]indole derivatives. NMR titration confirmed the suitability of the amine cavity for the complexation of methylammonium cations; moreover, the –NH– bridge function enables its further derivatization.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1668-9694.
- Supporting Information
Publication History
Received: 21 September 2021
Accepted after revision: 14 October 2021
Accepted Manuscript online:
14 October 2021
Article published online:
06 December 2021
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For selected books on calixarenes and their applications, see:
For selected reviews on various calixarene-based receptors, see:
Recently, other types of interesting rigid systems have been reported: