A Molecular Cage Accessed by Threefold Click Reaction of a C3v-Symmetric Triazido-Functionalized Tribenzotriquinacene.
J Org Chem
; 89(4): 2127-2137, 2024 Feb 16.
Article
em En
| MEDLINE
| ID: mdl-38270538
ABSTRACT
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.
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1
Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Revista:
J Org Chem
/
J. org. chem
/
Journal of organic chemistry
Ano de publicação:
2024
Tipo de documento:
Article