This article describes an enantioselective strategy for the synthesis of the kainoid component, (+)-allokainic acid using an organocatalytic approach. A cross-aldol reaction catalyzed by diphenylprolinol yielded a highly functionalized -lactam with excellent enantio- and diastereoselectivity, and the resulting hydroxy pyrrolidone was then utilized to synthesize Ganem's intermediate of (+)-allokainic acid. Krapcho decarboxylation and Wittig olefination were pivotal transformations towards the final -substituted Ganem's intermediate.
View Article and Find Full Text PDFA new series of syn-functionalised chiral hydroxy pyrrolidines and pyrrolidones containing α,β-contiguous stereocenters were synthesized via a diphenylprolinol-catalysed asymmetric cross aldol reaction. The synthesized compounds were characterised and evaluated for their α-glucosidase inhibitory potential. The hydroxy pyrrolidine series (9a-9i) was found to be selectively more potent against the α-glucosidase enzyme as compared to the pyrrolidone series (10a-10i).
View Article and Find Full Text PDFSeveral salicylidene-based colorimetric and fluorimetric anion sensors are known in the literature. However, our H-NMR experimental results (in DMSO-d) showed hydrolysis of imine (-N[double bond, length as m-dash]CH-) bonds in salicylidene-based receptors (SL, CL1 and CL2) in the presence of quaternary ammonium salts (-BuN) of halides (Cl and Br) and oxo-anions (HPO , HSO and CHCOO). The mono-salicylidene compound CL1 showed the most extensive -N[double bond, length as m-dash]CH- bond hydrolysis in the presence of anions.
View Article and Find Full Text PDFActa Crystallogr E Crystallogr Commun
August 2018
Compounds (I), CHNO, (II), CHNO and (III), CHNO are the products of three-component reactions between isatoic anhydride, the corresponding amine and 3-(5-methylfuran-2-yl)- or (furan-2-yl)-2-methyl-acryl-aldehyde. Compound (I) crystallizes in the monoclinic space group 2/, while compounds (II) and (III) are isostructural and crystallize in the ortho-rhom-bic space group . The tetra-hydro-pyrimidine ring in (I)-(III) adopts a conformation.
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