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A joint experimental and theoretical structural study of novel substituted 2,5-dioxo-1,2,3,4,5,6,7,8-octahydroquinolines

✍ Scribed by Margarita Suárez; Estael Ochoa; Yamila Verdecia; Beatriz Pita; Lourdes Morán; Nazario Martín; Margarita Quinteiro; Carlos Seoane; JoséL Soto; Hector Novoa; Norbert Blaton; Oswald M Peters

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
672 KB
Volume
55
Category
Article
ISSN
0040-4020

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✦ Synopsis

A series of substituted 2,5-dioxo-l,2,3,4,5,5,7,8-octahydroquinolines have been synthesised from Meidrum's acid and dimedone in the presence of different aldehydes by following an approach similar to the one developed by Hantzch. The structure of these compounds has been thoroughly studied by X-ray crystallographic analysis and semiempirieal (AMI) and ab initio (HF/3-21G) methods, and two favoured conformations are possible. A good agreement is found between the theoretical and experimental values. The most stable conformation (A) in the solid state is also that favoured in solution, according to the proton coupling constant determined from Karplus' and Altona's equations and tH NMR spectroscopic experiments.

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