Study of Meldrum's Acid Cyclization Reactions

The Journal of Physical Chemistry. a
Cristina TrujilloIsabel Rozas

Abstract

On the basis of the cyclization reactions reported by Danishefsky et al. of Meldrum's acid hydroxylethyl and anilinoethyl derivatives, the cyclization of the sulfamidomethylene and ureidomethylene derivatives was attempted without success. To understand the lack of reactivity of these compounds versus the successful cyclization of the ethyl derivatives, the corresponding mechanisms of reaction for both processes have been explored by means of MP2/6-311+G(d,p) calculations in an aqueous environment. The conformational analysis of all of these structures revealed that, while for the ethyl derivatives the minimum energy conformation corresponds to that of the cyclization initiating structure, for the methylene analogues the entrance channel conformations are substantially less stable than the energy minimum. Intramolecular hydrogen bonds were found in all of the energy minima as well as in the cyclization initiating conformations as determined by analysis of their electron density. The potential energy surfaces for the successful and unsuccessful cyclization processes were obtained at room temperature and 100 °C. Comparison of both processes allows rationalization that the lack of reactivity of the methylene derivatives can be the...Continue Reading

References

Aug 1, 1992·Archiv der Pharmazie·A HerreroA R Martínez Fernández
Aug 12, 2005·Chemical Reviews·Jacopo TomasiRoberto Cammi
Jun 1, 2007·Physical Chemistry Chemical Physics : PCCP·Isabel Rozas
Oct 1, 1948·Journal of the American Chemical Society·D DAVIDSON, S A BERNHARD
Dec 16, 2016·Journal of Medicinal Chemistry·Lai WeiYe Fang
Feb 17, 2017·Journal of the American Chemical Society·Sourabh MishraAaron Aponick
Mar 17, 2017·Journal of the American Chemical Society·Ricardo Palos PachecoJeanne E Pemberton

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