Synthesis and structural study of a series of amides derived from 4α- and 4β-amino-1-azaadamantanes as potential 5-HT3receptor antagonists

Autor: Iriepa, I, Villasante, F.J, Gálvez, E, Bellanato, J
Zdroj: Journal of Molecular Structure; October 1999, Vol. 509 Issue: 1-3 p105-114, 10p
Abstrakt: A series of amides derived from 4α-(2b–5b) and 4β-amino-1-azaadamantane (2a–5a) were synthesized and studied by IR, 1H, 13C, 2D NMR spectroscopy and NOE 1D experiments. The combined use of COSY, 1H–13C correlation spectra and double resonance experiments helped in the unambiguous and complete assignment of the bicyclic carbon and proton resonances. IR, 1H and 13C NMR data show the presence of an intramolecular N–H⋯O–CH3hydrogen bond in compounds 3aand 3b. Moreover, the IR spectra of compounds 4aand 4bshow a strong intermolecular hydrogen bond N–H (indole)⋯N.
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