200063-53-2

Upstream product

• 67067-96-3 ethyl ester of N-benzyl-α-phenylglycine 
• 2882-19-1 ethyl 2-phenyl-2-bromoacetate 
• 100-46-9 benzylamine 
• 101-97-3 Ethyl 2-phenylethanoate 
• 124-38-9 carbon dioxide 
• 1594106-07-6 N-benzyl-N-(methoxy(phenyl)methyl)acetamide 
• 67627-99-0 N-benzyliden-α-phenyl-glycine methyl ester 
• 96011-42-6 methyl 2-(N-benzylacetamido)-2-phenylacetate 

Downstream Products

• 1304779-92-7 3-(1-benzyl-2-methyl-5-phenyl-1H-pyrrol-3-yl)-1H-indole 
• 1304779-93-8 3-(1-benzyl-2-methyl-5-phenyl-1H-pyrrol-3-yl)-1-methyl-1H-indole 
• 1304779-97-2 2-(1-benzyl-2-methyl-5-phenyl-1H-pyrrol-3-yl)-1-(phenylsulfonyl)-1H-indole 
• 1448819-78-0 1-benzyl-5-methyl-2,3-diphenyl-1H-pyrrole 
• 141334-88-5 1-benzyl-2-methyl-3,5-diphenyl-1H-pyrrole 

Relevant academic research and scientific papers

Synthesis of Heteroaryl-Substituted Pyrroles via the 1,3-Dipolar Cycloaddition of Unsymmetrical Münchnones and Nitrovinylheterocycles

A series of furanyl-, thiophenyl-, and pyrrolo-substituted pyrroles were prepared via the 1,3-dipolar cycloaddition of unsymmetrical münchnones and nitrovinylheterocycles. The regiochemical outcome of the furan and thiophene cycloadditions compares favorably to previously reported cycloadditions with β-nitrostyrene, while the nitrovinylpyrrole cycloadditions mirror the results observed with nitrovinylindole.

2-Bromo-6-isocyanopyridine as a Universal Convertible Isocyanide for Multicomponent Chemistry

The development of 2-isocyanopyridines as novel convertible isocyanides for multicomponent chemistry is reported. Comparison of 12 representatives of this class revealed 2-bromo-6-isocyanopyridine as the optimal reagent in terms of stability and synthetic efficiency. It combines sufficient nucleophilicity with good leaving group capacity of the resulting amide moiety under both basic and acidic conditions. To demonstrate the practical utility of this reagent, an efficient two-step synthesis of the potent opioid carfentanil is presented.

Synthesis of arylglycines from CO2 through α-amino organomanganese species

In the presence of three readily available chemicals, Mn powder, BF 3·OEt2, and LiCl, N-acyl-N,O-acetals were successfully converted into the corresponding α-amino acids (arylglycine derivatives) under 1 atm of a CO2 atmosphere in high yields. The LiCl additive is necessary in order to increase the solubility and the nucleophilicity of an organomanganese intermediate. The products thus obtained were transformed into free α-amino acids in two steps.

What controls regiochemistry in 1,3-dipolar cycloadditions of Muenchnones with nitrostyrenes?

The distinct experimentally observed regiochemistries of the reactions between mesoionic muenchnones and β-nitrostyrenes or phenylacetylene are shown by DFT/BDA/ETS-NOCV analyses of the transition states to be dominated by steric and reactant reorganization factors, rather than the orbital overlap considerations predicted by Frontier Molecular Orbital (FMO) Theory.

Regioselective 1,3-dipolar cycloaddition reactions of unsymmetrical munchnones (1,3-oxazolium-5-olates) with 2- and 3-nitroindoles. A new synthesis of pyrrolo[3,4-b]indoles

The unsymmetrical mesoionic munchnones 13 (3-benzyl-2-methyl-4-phenyl-1,3-oxazolium-5-olate) and 14 (3-benzyl-4-methyl-2-phenyl-1,3-oxazolium-5-olate) react with the N-protected 2- and 3-nitroindoles 1 (ethyl 2-nitroindole-1-carboxylate), 6 (3-nitro-1-(phenylsulfonyl)indole), and 17 (ethyl 3-nitroindole-carboxylate) in refluxing THF to afford in good to excellent yields the pyrrolo[3,4-b]indoles 15 (2-benzyl-1-methyl-3-phenyl-4-carboethoxy-2,4-dihydropyrrolo[3,4-b]indole), 16 (2-benzyl-3-methyl-1-phenyl-4-carboethoxy-2,4-dihydropyrrolo[3,4-b]indole), 18 (2-benzylmethyl-3-phenyl-4-(phenylsulfonyl)-2,4-dihydropyrrolo[3,4-b]indole), and 19 (2-benzyl-3-methyl-1-phenyl-4-(phenylsulfonyl)-2,4-dihydropyrrolo[3,4-b]indol e). In several cases the regiochemistry, which is opposite to that predicted by FMO theory, is very high and leads essentially to a single pyrrolo[3,4-b]indole; e.g., 6+ 13→19 in 74% yield. (C) 2000 Elsevier Science Ltd.

Novel formation and crystal structure of 2-(2,2,2-trifluoroethylidene)-6-trifluoro-methyl-2,3-dihydro-4H-1,4-oxazin-3- ones from N-acetyl-N-alkyl-α-amino acids

The title compounds (2a-g) were formed from N-acetyl-N-alkyl-α-amino acids (1a-g) on treatment with trifluoroacetic anhydride in the presence of pyridine. The structure of the product (2a) was determined by single crystal X-Ray analysis.