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N-arylhexahydropyrimidines. Part 1. Synthesis and 1H NMR characterization of 1,3-Di and 1,2,3-trisubstituted derivatives

✍ Scribed by Isabel A. Perillo; María B. García; Juan Á. Bisceglia; Liliana R. Orelli

Publisher
Journal of Heterocyclic Chemistry
Year
2002
Tongue
English
Weight
76 KB
Volume
39
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

A series of N‐arylhexahydropyrimidines la‐1 were synthesized by condensation of N‐aryl‐N'‐alkyl‐ (or aryl)‐1,3‐propanediamines 2a‐h with aldehydes. Reactions with formaldehyde proceeded in hydroalcoholic solution, while condensation with aromatic aldehydes required in general the use of activated molecular sieves. ^1^H NMR spectra of compounds la‐1 were analyzed and the results correlated with their conforma‐tional features. Derivatives devoid of a 2‐substituent la‐g show fast ring reversal and N‐inversion. The presence of a 2‐aryl group shifts the ring reversal equilibrium towards conformations where the 2‐aryl substituent is equatorial. Differential assignment of axial and equatorial hydrogens in these compounds was made on the basis of coupling constants and chemical shift values. In compound 1k spectral data suggest the axial orientation of the N‐methyl group. Such findings were confirmed in the corresponding NOESY spectrum.

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