期刊
CHEMICAL COMMUNICATIONS
卷 46, 期 14, 页码 2459-2461出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/b926072b
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资金
- Skaggs Institute for Research
- National Institutes of Health [GM 27932]
- Skaggs Postdoctoral Fellow
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R01GM027932, R37GM027932] Funding Source: NIH RePORTER
The condensation of a Kemp's triacid derivative with a diamino resorcinarene yielded a cavitand with the deepest cavity prepared to date featuring an inwardly-directed carboxylic acid. The extended 6,7-diaminoquinoxaline wall bearing the acid allowed accommodation of large amines, such as 1-adamantanemethyl-amine, as well as smaller amines such as triethylamine. Adamantyl and cyclohexyl isocyanides are also bound in the deep cavitand in a way that positions the isonitrile function near the carboxylic acid group. Reaction occurs inside the cavity at ambient temperature to form the respective N-acylformamides. Low concentrations of the transient O-acyl isoamide intermediate were detected by (1)H NMR and IR spectroscopy.
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