Synthesis 2022; 54(05): 1301-1308
DOI: 10.1055/a-1668-9694
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Azide Decomposition as a Pathway to Intramolecularly Upper-Rim-Bridged Calix[4]arenes

Martin Tlustý
a   Department of Organic Chemistry, University of Chemistry and Technology, Prague, Technická 5, 16628 Prague 6, Czech Republic
,
Václav Eigner
b   Department of Solid State Chemistry, University of Chemistry and Technology, Prague, Technická 5, 16628 Prague 6, Czech Republic
,
Pavel Lhoták
a   Department of Organic Chemistry, University of Chemistry and Technology, Prague, Technická 5, 16628 Prague 6, Czech Republic
› Author Affiliations
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



Publication History

Received: 21 September 2021

Accepted after revision: 14 October 2021

Publication Date:
14 October 2021 (online)

© 2021. Thieme. All rights reserved

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