Jong Woo Bae

Chemoselective reduction of nitroaromatics to anilines using decaborane in methanol

Nitrobenzenes were chemoselectively reduced to the corresponding anilines using decaborane (B10H14) in the presence of Pd/C and two drops of acetic acid at reflux under nitrogen atmosphere in high yields.

Reduction of ketones to alcohols using a decaborane/pyrrolidine/cerium(III) chloride system in methanol

Abstract Decaborane was found to be an effective agent for the chemoselective reduction of ketones to alcohols in the presence of pyrrolidine and cerium(III) chloride heptahydrate in methanol.

Synthesis of pyrido[2,3-d]pyrimidines via palladium-catalyzed reaction of iodouracil with acetylenes

Abstract The reactions of iodouracils having a formamidine or acetamidine moiety 1 with various acetylenes 2 in DMF at 120°C using potassium carbonate and a catalytic amount of palladium acetate gave a mixture of pyrido[2,3- d ]pyrimidine derivatives in good to high yields. Addition of lithium chloride to the reaction solution resulted in a change of reaction selectivity.

A one-pot synthesis of N-alkylaminobenzenes from nitroaromatics: reduction followed by reductive amination using B10H14

N-Alkylaminobenzenes were prepared in a simple and efficient one-pot synthesis by reduction of nitrobenzenes followed by reductive amination with decaborane (B10H14) in the presence of 10% Pd/C.

Palladium-Catalyzed Coupling Reaction of Iodouracil Having Acetamidine Moiety with Olefins

Abstract The reaction of 6-[1-Aza-2-(dimethylamino)prop-l-enyl]-5-iodo-1,3-dimethyluracil (3) with various olefins in the presence of a catalytic amount of Pd(OAc)2 and 1.5 equiv. of K2CO3 in DMF at 120 °C gave the pyrido[2,3-d]pyrimidine derivatives (5a-b and 7a-d) in moderate to high yield.

A reductive amination of carbonyls with amines using decaborane in methanol

Aldehydes and ketones were easily converted to the corresponding amines by the reaction of amines in methanol using decaborane (B10H14) at room temperature under nitrogen. The reaction is simple and efficient.

REDUCTIVE METHYLATION USING DECABORANE IN METHANOL

Amines (primary and secondary) were methylated to the corresponding tertiary amine using 37% formaldehyde and decaborane in methanol at room temperature under nitrogen in high yields.

Fischer's base as a protecting group: protection and deprotection of 2-hydroxybenzaldehydes

Abstract The hydroxyl and aldehyde groups of 2-hydroxybenzaldehydes were protected by the reaction with Fischers base and deprotected by the ozonolysis in methanol at −78°C to give the corresponding 2-hydroxybenzaldehydes in good to high yields.

Synthesis of 7-Hydroxyspiropyran

Abstract The 7-acetoxyspiropyrans (4a and 4b) have been prepared by the reaction of Fischers bases (3) with 2,4-diacetoxybenzaldehyde in refluxing ethanol in moderate yields. The acetyl group of 7-acetoxy-spiropyran 4a was easily removed to give a 7-hydroxyspiropyran 6 in high yield under the basic condition.

An Efficient and Convenient Synthesis of 5-Formylsalicylaldehyde

Abstract 5-Formylsalicylaldehyde 1, which is a key intermediate of spiropyran dye and a recently developed insulin sensitivity enhancer (ISE) compounds, was prepared from 5-iodosalicylaldehyde by the palladiumcatalyzed coupling reaction with ethyl acrylate followed by ozonolysis in high overall yield (92%).