Concatenated Batch and Continuous Flow Procedures for the Upgrading of Glycerol-Derived Aminodiols via N-Acetylation and Acetalization Reactions

An unprecedented two-step sequence was designed by combining batch and continuous flow (CF) protocols for the upgrading of two aminodiol regioisomers derived from glycerol, i.e., 3-amino-1,2-propanediol and 2-amino-1,3-propanediol (serinol). Under batch conditions, at 80–90 °C, both substrates were quantitatively converted into the corresponding amides through a catalyst-free N-acetylation reaction mediated by an innocuous enol ester as isopropenyl acetate (iPAc). Thereafter, at 30–100 °C and 1–10 atm, the amide derivatives underwent a selective CF-acetalisation in the presence of acetone and a solid acid catalyst, to afford the double-functionalized (amide-acetal) products.

Post-polymerization modification of polymethacrylates enabled by keto–enol tautomerization

We report a post-polymerization modification strategy to functionalize methacrylic copolymers through enol-ester transesterification.

Crystal structure determination of rac-11′-(1-acetyl-1H-indazol-3-yl)-11′,11a′-dihydro-10′H,17′H-spiro[indene-2,18′-[5a,16b]methanotriindeno[1,2-b:1′,2′-d:2′′,1′′-g]oxocine]-1,3,10′,12′,17′(10a′H)-pentaone acetonitrile 1.5-solvate

The title compound, C46H26N2O7·1.5CH3CN, is the aldol condensation product of bindone with indazole-3-carbaldehyde followed by double intermolecular cyclization. The asymmetric unit, which has monoclinic P21/c symmetry, contains two independent molecules of the title compound and three acetonitrile molecules. The title molecule comprises a central eight-membered ring, which contains an enol–ester, from which five arms extend. The arms exhibit intermolecular interactions within the crystal lattice between molecules of the title compound and with co-crystallized solvent molecules (acetonitrile).

Design, microwave-assisted synthesis, bioactivity and SAR of novel substituted 2-phenyl-2-cyclohexanedione enol ester derivatives

Based on the structure–activity relationship and active substructure combination, a novel class of substituted 2-phenyl-2-cyclohexanedione enol ester derivatives was designed for use as potential herbicide safeners.

Molecular structure of a brominated 2-benzazepinone – a crucial intermediate in the synthesis of novel chemokine CCR2 receptor antagonists

Chemokines (chemoattractant cytokines) together with their receptors represent key players in inflammatory processes. In order to develop novel chemokine CCR2 and CCR5 receptor antagonists, 2-benz-azepin-1-one 5 was prepared, which showed promising CCR2 affinity. During the synthesis, regioisomeric bromo substituted β-keto esters 4a and 4b had to be separated. A crystal structure determination of the regioisomer 4b displayed unequivocally the bromine atom in the 7-position and the existence of 4b as the enol ester tautomer. Although the 7-membered azepine ring is rather flat, it is distorted around the 3-methylene moiety.