Heterocyclic synthesis via the intramolecular acylation of enamines derived from amino acids

Abstract

A general heterocyclic synthesis using enamines derived from amino acids is described. The use of salts of amino acids in the enamine-forming step is developed. The preparations of dihydroorcinol and dehydroproline, potential starting materials for the heterocyclic synthesis, are described. Asymmetric induction, ultimately observed in the heterocycle, caused by the chiral amino acids, is discussed.

6 Hz Active Anticonvulsant Fluorinated N-Benzamide Enaminones and Their Inhibitory Neuronal Activity

“…The synthetic procedure involved amination of the respective β-diketones to generate the methylated enaminone intermediates, followed by acylation with the respective substituted acyl chloride to provide target compounds 4a – 9b , (Figure 3) [9,15,20]. We obtained all of the final compounds in moderate to good yields (14%–63%), as shown in Table 1.…”

Crystal structures of proline-derived enamines

“…Indeed, proline-derived vinylogous amides (or enaminones) have been reported previously and characterized spectroscopically as enamines (20)(21)(22)(23). More important for the present discus- sion is that such vinylogous amides may be considered transition state models of a proline enamine engaging in the reaction with an electrophile (Fig.…”

A Substituted Anilino Enaminone Acts as a Novel Positive Allosteric Modulator of GABAA Receptors in the Mouse Brain

“…2. The ␤-hydroxy keto tert-butoxy ester was prepared as reported previously (Friary et al, 1973;Edafiogho et al, 1992;Scott et al, 1993). The enaminone structures were confirmed via NMR analyses at 400 MHz.…”