Hong Jung Lee

Synthesis of 3-quinolinecarboxylic acid esters from the Baylis–Hillman adducts of 2-halobenzaldehyde N-tosylimines

Abstract 3-Quinolinecarboxylic acid ethyl esters 4 were prepared from 1 , the Baylis–Hillman adducts of o -halobenzaldehyde N -tosylimines, in a one-pot reaction.

Synthesis of enantiomerically enriched Baylis–Hillman alcohols from their acetates: combination of kinetic resolution during the salt formation with (DHQD)2PHAL and following asymmetric induction during hydrolysis with NaHCO3 as a water surrogate

Abstract Enantiomerically enriched Baylis–Hillman alcohols 2a – d ( S ) were prepared in 25–42% yields with optical purities of 54–92% ee by using the combined concept of kinetic resolution during the salt formation of racemic Baylis–Hillman acetates 1a – d with (DHQD) 2 PHAL and the asymmetric induction during the S N 2′ type reaction with sodium bicarbonate as a water surrogate.

Synthesis of stereochemically defined (E)-cinnamyl alcohol derivatives from the Baylis–Hillman adducts

Abstract The reaction of the Baylis–Hillman adducts 1a – g and trifluoroacetic acid at 30–70°C gave the rearranged cinnamyl alcohols 2a – g stereoselectively in moderate yields.

Friedel-Crafts reaction of the Baylis-Hillman adducts of N-tosylimine derivatives

Friedel-Crafts reaction of aromatic compounds with the Baylis-Hillman adducts of N-tosylimine derivatives in the presence of sulfuric acid provided a stereoselective methodology for the preparation of 2-benzylsubstituted olefins in moderate yields.

A facile one-pot preparation of isothiocyanates from aldoximes

Abstract Isothiocyanates 2a-1 were prepared in excellent yields in a one-pot reaction from aldoxime derivatives 1a-1 by successive treatment of aldoxime with N -chlorosuccinimide (NCS), thiourea, and triethylamine. The use of HCl / DMF / Oxone system in the reaction instead of NCS was equally effective.

The reaction of the Baylis-Hillman adducts of N-tosylimines with N,N-dimethylformamide dimethylacetal

Abstract The reaction of N,N -dimethylformamide dimethylacetal (DMF-DMA) and the Baylis-Hillman adducts of N -tosylimines afforded N -methyl- N -tosyl allylic amine derivatives stereoselectively in moderate yields.

Decarbonylative diarylation reaction of N-tosylated α-amino acids

Abstract The reaction of various N -tosylated α-amino acids with arenes in the presence of sulfuric acid afforded the corresponding diarylated derivatives in moderate yields, which were generated via decarbonylative arylation followed by Friedel-Crafts reaction of the generated tosylamide derivatives.

Friedel-Crafts Type Reactions of Some Activated Cyclic Ketones with Phenol Derivatives

Abstract Friedel-Crafts type reactions of phenol derivatives with some cyclic ketones such as ninhydrin (1), alloxan (2), isatin (3), and parabanic acid (4) were examined. 2-Monoaryl- and 2,2-diaryl-1,3-indanedione derivatives were obtained depending on the acid catalyst in the cases of ninhydrin and alloxan. In the case of isatin, the corresponding diarylated derivative was obtained as the sole product in high yields. Parabanic acid was unreactive under the reaction conditions.

Formation of Benzo[b]Indeno [2,1-d]Furanone Ring System During Alkylation of 2-(2-Hydroxyaryl)-2-Hydroxy-1,3-Indanedione Derivatives

Abstract During alkylation of 2-(2-hydroxyaryl)-2-hydroxy-1,3-indanedione derivatives, O-alkylated benzo[b]indeno[2,1-d]furanone derivatives were formed in appreciable amounts.

The Reaction of Ninhydrin with Trimethylbenzenes under Friedel-Crafts Reaction Conditions

Abstract The reaction of ninhydrin with 1,2,3- and 1,2,4-trimethylbenzene in the presence of H2SO4 or AlCl3 afforded 2-monoaryl and 2,2-diaryl-1,3-indanedione derivatives as the major products. With 1,3,5-trimethylbenzene as the arene nucleophile, either a reduction product or an indenoindanone derivative was obtained depending upon the catalyst employed in the reaction.