1008934-91-5

Upstream product

• 15028-44-1 DL-phenylalanine methyl ester 
• 2284-20-0 4-Methoxyphenyl isothiocyanate 
• 150-30-1 Phenylalanine 

Relevant academic research and scientific papers

Unprecedented one-pot chemocontrolled entry to thioxoimidazolidinones and aminoimidazolones: Synthesis of kinase inhibitor Leucettamine B

A novel and highly chemoselective protocol for the construction of thioxoimidazolidinone and aminoimidazolone frameworks was explored, and the influence of the reaction conditions on product formation was studied to establish two distinct approaches for their selective formation. In this one-pot reaction, ambient temperature generally resulted in the formation of thioxoimidazolidinones, whereas microwave irradiation provided aminoimidazolones exclusively. An attempt to elucidate the observed chemoselectivity is described, and the products were confirmed by X-ray studies. One-pot synthesis toward Leucettamine B, a marine alkaloid, was achieved on the basis of this protocol.

Asymmetric Synthesis of Adjacent Tri- and Tetrasubstituted Carbon Stereocenters: Organocatalytic Aldol Reaction of an Hydantoin Surrogate with Azaarene 2-Carbaldehydes

A bifunctional amine/squaramide catalyst promoted direct aldol addition of an hydantoin surrogate to pyridine 2-carbaldehyde N-oxides to afford adducts bearing two vicinal tertiary/quaternary carbons in high diastereo- and enantioselectivity (d.r. up to >20:1; ee up to 98 %) is reported. Acid hydrolysis of adducts followed by reduction of the N-oxide group yields enantiopure carbinol-tethered quaternary hydantoin-azaarene conjugates with densely functionalized skeletons. DFT studies of the potential energy surface (B3LYP/6–31+G(d)+CPCM (dichloromethane)) of the reaction correlate the activity of different catalysts and support an intramolecular hydrogen-bond-assisted activation of the squaramide moiety in the transition state of the catalytic reaction.

An efficient method for synthesis of thiohydantoins with α-amino esters under microwave irradiation

An efficient and simple way for synthesis of thiohydantoins is reported. In the absence of any additional catalysts, a series of thiohydantoins were synthesized with amino esters and isothiocyanates in aqueous medium under microwave irradiation. Excellent isolated yields (up to 98 %) were obtained under mild conditions.

Microwave assisted synthesis of 1,3,4-oxadiazole/thiohydantoin hybrid derivatives via dehydrative cycliztion of semicarbazide

A series of compounds containing both 1,3,4-oxadiazole and thiohydantoin were synthesized as a promising scaffold for application in medicinal chemistry. The key step of the synthesis is a microwave-assisted cyclization of semicarbazides possessing a thiohydantoin moiety at one of the acyl termini using POCl3 as a dehydrating reagent. A wide range of semicarbazides were prepared through the substitution of hydrazides with an N-acylated thiohydantoin derived from the cyclization of the corresponding isothiocyanate with an amino acid and subsequent N-acylation of the resultant thiohydrantion. Consequently, the 58 number of 1,3,4-oxadiazole derivatives having a thiohydantoin substituent were prepared in good overall yields. Thiohydantoin 134-Oxadiazole Semicarbazide Microwave Amino acid Acknowledgments. This research was conducted under the Industrial Infrastructure Program for Fundamental Technologies and Institute for Advancement of Technology through the Inter-ER Cooperation Projects (R0002016) which are funded by the Ministry of Trade, Industry & Energy, Korea to YDG and Open Translational Research Center for Innovative Drug (2012M3A9C1053532) which are funded by National Research Foundation of Korea.