67909-04-0

Upstream product

• 2301-40-8 3-benzylhydantoin 
• 118004-65-2 1-Benzyl-3-(2-trimethylsilanyl-ethoxymethyl)-1,3-dihydro-imidazol-2-one 
• 3173-56-6 benzyl isothiocyanate 
• 100-39-0 benzyl bromide 
• 67909-05-1 N-(2,2-diethoxyethyl)[benzylamino]carboxamide 
• 91558-02-0 ethyl 2-(3-benzylureido)acetate 
• 85369-80-8 3-benzyl-4-hydroxy-imidazolidin-2-one 

Downstream Products

• 475474-07-8 3-[4-(3-benzyl-2-oxo-2,3-dihydro-imidazol-1-yl)-phenyl]-2-(9-phenyl-9H-fluoren-9-ylamino)-propionic acid tert-butyl ester 
• 2385-38-8 1-benzyl-2,3,4,5-tetrahydroimidazol-2-one 
• 732297-06-2 (S)-3-[4-(3-Benzyl-2-oxo-2,3-dihydro-imidazol-1-yl)-phenyl]-2-[((R)-2-methyl-tetrahydro-furan-2-carbonyl)-amino]-propionic acid methyl ester 
• 790208-55-8 (S)-2-Amino-3-[4-(3-benzyl-2-oxo-2,3-dihydro-imidazol-1-yl)-phenyl]-propionic acid 

Relevant academic research and scientific papers

Chemoselective Electrosynthesis Using Rapid Alternating Polarity

Challenges in the selective manipulation of functional groups (chemoselectivity) in organic synthesis have historically been overcome either by using reagents/catalysts that tunably interact with a substrate or through modification to shield undesired sites of reactivity (protecting groups). Although electrochemistry offers precise redox control to achieve unique chemoselectivity, this approach often becomes challenging in the presence of multiple redox-active functionalities. Historically, electrosynthesis has been performed almost solely by using direct current (DC). In contrast, applying alternating current (AC) has been known to change reaction outcomes considerably on an analytical scale but has rarely been strategically exploited for use in complex preparative organic synthesis. Here we show how a square waveform employed to deliver electric current - rapid alternating polarity (rAP) - enables control over reaction outcomes in the chemoselective reduction of carbonyl compounds, one of the most widely used reaction manifolds. The reactivity observed cannot be recapitulated using DC electrolysis or chemical reagents. The synthetic value brought by this new method for controlling chemoselectivity is vividly demonstrated in the context of classical reactivity problems such as chiral auxiliary removal and cutting-edge medicinal chemistry topics such as the synthesis of PROTACs.

Triazole compounds as well as preparation method and application thereof

The invention belongs to the technical field of medicinal chemistry, and particularly relates to triazole compounds and a preparation method and application thereof. The triazole compounds have excellent LPAR1 antagonistic activity and selectivity, are lo

HMG-CoA reductase inhibitors

Compounds are provided of the following structure are HMG CoA reductase inhibitors and thus are active in inhibiting cholesterol biosynthesis, modulating blood serum lipids, for example, lowering LDL cholesterol and/or increasing HDL cholesterol, and trea

2-IMIDAZOLONE AND 2-IMIDAZOLIDINONE HETEROCYCLIC INHIBITORS OF TYROSINE PHOSPHATASES

Compounds and compositions are provided for modulating the activity of protein tyrosine phosphatases. The compounds for use in the compositions and methods provided herein have formulae (I) Protein tyrosine hosaphatase, including PTB-1B, mediated diseases and disorders include diabetes including Type 1 and Type 2 diabetes (and associated complications such as hypertension, ischemic diseases of the large and small blood vessels, blindness, circulatory problems, kidney failure and atherosclerosis), syndrome X, methabolic syndrome, glucose intolerance, insulin resistance, obesity, cancer, neurodegenerative diseases.

METALATIONS OF IMIDAZOLES. (POLY)FUNCTIONALIZATION AND CONVERSIONS TO IMIDAZOLONES

N-SEM protected imidazoles can be sequentially derivatized at the 2- and then 5-positions in a 1-pot operation.Quenching with selected peroxides following initial lithiation leads directly to imidazolones.

Effect of structural modification of the hydrantoin ring on anticonvulsant activity

Selectively substituted hydantoins (15 examples), 4-hydroxy-2-imidazolidinones (13 examples), 2-imidazolones (10 examples), 2-imidazolidinones (four examples), vicinal diamines (two examples), and simple amino acid derivatives (four examples) have been pr

Selective Reductions of 3-Substituted Hydantoins to 4-Hydroxy-2-imidazolidinones and Vicinal Diamines

N3-Substituted hydantoins (1) have been shown to undergo LiAlH4 reduction (THF, room temperature, 2 days) to give 4-hydroxy-2-imidazolidinones (3) in good yields.Reduction of 3,5-disubstituted hydantoins in which an aliphatic substituent was present at nitrogen 3 led to the preferential formation of the cis adduct 3.Conversely, disubstituted hydantoins possessing an aryl moiety at nitrogen 3 gave the trans derivative 3 as the major product.Treatment of the N3-substituted hydantoins (1) under more vigorous conditions (THF, reflux, 3 days) led to selective ring opening of 1 to yield N-methylethylenediamines (7).The scope of both of these reductive processes has been explored, and explanations are offered to account for the observed results.Full spectral (infrared, 1H and 13C NMR, and mass spectra) data on all three classes of compounds (1, 3, and 7) have been collected.Together this information provides a consistent data set which is useful in structure elucidation.Moreover, various NMR aids have been discerned for the isomeric cis- and trans-4-hydroxy-2-imidazolidinones (3) which permitted stereochemical assignments for these compounds.