75152-19-1

Upstream product

• 13214-64-7 N-(4-methoxybenzoyl)glycine 
• 75152-16-8 (4-Methoxy-benzoylamino)-acetic acid 4-nitro-phenyl ester 
• 51220-57-6 ethyl 2-(4-methoxybenzamido)acetate 
• 100-07-2 4-methoxy-benzoyl chloride 

Downstream Products

• 32603-60-4 2-(4-methoxy-phenyl)-4-[2-(1-methyl-1H-naphtho[1,2-d]oxazol-2-ylidene)-ethylidene]-4H-oxazol-5-one 
• 32603-59-1 2-(4-methoxy-phenyl)-4-[2-(3-methyl-3H-naphtho[2,1-d]oxazol-2-ylidene)-ethylidene]-4H-oxazol-5-one 
• 13214-64-7 N-(4-methoxybenzoyl)glycine 
• 1206983-16-5 2-(2-(4-methoxyphenyl)oxazol-5-yl)acetonitrile 

Relevant academic research and scientific papers

Synthesis, cytotoxicity, and docking study of novel 1-naphthyl-5-aryl-1H-1,2,4-triazole-3-carboxamides

A new series of 1-naphthyl-5-aryl-1H-1,2,4-triazole-3-carboxamide derivatives were synthesized and structurally proved by 1H and 13C NMR along with high-resolution mass spectrometry. The cytotoxic activity of the newly synthesized compounds was evaluated. Compounds showed a pronounced inhibitory effect against cellular localization of tubulin. Flow cytometric analysis showed that Hep-G2 cells treated indicated a predominated growth arrest at the G2/M-phase compared to that of S-phase. Molecular modeling study using MOE program indicated that most of the target compounds showed good binding with the colchicine-binding site of β-subunit of tubulin with the binding free energy (?G) values of about 42?kJ/mol. Graphical abstract: [Figure not available: see fulltext.].

Catalytic Asymmetric Synthesis of anti-α,β-Diamino Acid Derivatives

A novel approach to chiral anti-α,β-diamino acid derivatives through tandem orthogonal organocatalysis has been developed. Chiral phosphoric acid catalysts control the chemo-, regio-, and stereoselective addition of hydroxylamines to alkylideneoxazolones, while a phosphine catalyst promotes the isomerization of Z- alkylideneoxazolones to the more reactive E- alkylideneoxazolones. (Chemical Equation Presented).

Synthesis of di- and tri-substituted imidazole-4-carboxylates via PBu3-mediated [3+2] cycloaddition

Some new di- and trisubstituted imidazole-4-carboxylates were prepared from amidoacetic acids 3 in the present report. The key step to establish such imidazole- 4-carboxylates stemmed from the PBu3-mediated [3+2] cycloaddition between in situ-generated Δ2-oxazolinone 4 and ethyl cyanoformate6. Our results indicated that trisubstituted imidazoles 7-20 were afforded in better yields than those of disubstituted imidazoles 21-27. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications1 to view the free supplemental file. Copyright Taylor & Francis Group, LLC.

One-pot synthesis of 2,4,5-trisubstituted oxazoles from N-acyl amino acids by a combination of cyclodehydration with N,N′-diisopropylcarbodiimide and Wittig olefination

By a combination of cyclodehydration of N-acyl amino acids with N,N′-diisopropylcarbodiimide (DIC) and non-classical Wittig olefination of the resultant 5(4H)-oxazolones with Ph3PCHCN and Ph 3PCHCOOEt, 5-oxazoleacetonitriles and 5-oxazoleacetates were synthesized in one-pot in 41-85% and 57-70% yields, respectively.

A kinetic study of the base-catalyzed dimerization of 5(4H)-oxazolones

The effects of the substituent at position-2 and kind of the base on the rate of the base-catalyzed dimerization of 5(4H)-oxazolones have been investigated. The electrondonating and strong steric effect of the substituent at position-2 reduce markedly the proclivity of 5(4H)-oxazolones to dimerization. The following catalytic activity sequence of the bases has been found: DBU >> Et3N > (i-Pr)2EtN.

Structure-Reactivity Studies on the Equilibrium Reaction between Phenolate Ions and 2-Aryloxazolin-5-ones: Data Consistent with a Concerted Acyl-Group-Transfer Mechanism

The rate and equilibrium constants for the reaction between phenolate anions and 2-aryloxazolin-5-ones have been measured as a function of the structures Ar and Ar'.The change in "effective" charge on both phenol-leaving oxygen and endocyclic oxygen from ground to transition state, as determined from the relevant Broensted parameters, is substantial and essentially additive consistent with a concerted displacement mechanism.The stepwise mechanism requires a small change in effective charge on the phenol oxygen because departure of phenolate ion from the tetrahedral intermediate cannot be rate limiting.Hydroxide ion attack on the C-5 atom of the oxazolinone to yield a benzoylglycine has a Hammett ?- dependence which can only arise from a concerted displacement; the rate-limiting step for the stepwise mechanism is the addition of hydroxide and the transition state of the rate-limiting step will therefore not involve much endocyclic C-O bond fission.An inverse deuterium oxide solvent isotope effect indicates that the observed general-acid catalysis has a specific-acid/nucleophilic mechanism; both hydroxide and oxonium ion catalysis are demonstrated by using 18O-labeling experiments to involve nucleophilic attack at the carbonyl (C-5) center.The equilibrium constant for reaction of azide ion with 2-phenyloxazolin-5-ones has been measured; it is suggested that the absence of racemization during azide coupling in peptide synthesis is related to the very unfavorable equilibrium constant for oxazolinone formation compared with that of activated oxygen esters.