Unexpected diastereotopic behaviour in the 1H NMR spectrum of 1,4-dihydropyridine derivatives triggered by chiral and prochiral centres

Abstract

1,4-dihydropyridine derivatives constitute an important pharmacological group for the treatment of cardiovascular diseases. We have synthesised a series 4-(5′-nitro-2′-furyl)-1,4-dihydropyridine derivatives, which were characterised by 1H-NMR. We have found that carboethoxy groups at the C-3 and C-5 on the 1,4-dihydropyridine ring show a much more complex signal in the 1H NMR spectra, either when C-4 is a pseudo-prochiral or a chiral centre. ©2005 Sociedade Brasileira de Química.