A joint experimental and theoretical structural study of novel substituted2,5-dioxo-1,2,3,4,5,6,7,8-octahydroquinolines

Citation
M. Suarez et al., A joint experimental and theoretical structural study of novel substituted2,5-dioxo-1,2,3,4,5,6,7,8-octahydroquinolines, TETRAHEDRON, 55(3), 1999, pp. 875-884
Citations number
27
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
3
Year of publication
1999
Pages
875 - 884
Database
ISI
SICI code
0040-4020(19990115)55:3<875:AJEATS>2.0.ZU;2-C
Abstract
A series of substituted 2,5-dioxo-1,2,3,4,5,5,7,8-octahydroquinolines have been synthesised from Meldrum's acid and dimedone in the presence of differ ent aldehydes by following an approach similar to the one developed by Hant zch. The structure of these compounds has been thoroughly studied by X-ray crystallographic analysis and semiempirical (AM1) and ab initio (HF/3-21G) methods, and two favoured conformations are possible. A good agreement is f ound between the theoretical and experimental values. The most stable confo rmation (A) in the solid state is also that favoured in solution, according to the proton coupling constant determined from Karplus' and Altona's equa tions and H-1 NMR spectroscopic experiments. (C) 1998 Elsevier Science Ltd. All rights reserved.