7662-79-5

Upstream product

• 40682-54-0 ethyl N-benzylideneglycinate 
• 108-24-7 acetic anhydride 
• 7662-78-4 N-acetyl-N-benzylglycine tert-butyl ester 
• 7732-18-5 water 
• 74471-68-4 sodium N-benzylideneglycinate 
• 6436-91-5 ethyl N-acetyl-N-benzylaminoacetate 
• 7662-76-2 tert-butyl 2-(benzylamino)acetate 
• 100-46-9 benzylamine 
• 1011729-20-6 N-benzyl-N-[2-(1H-indolyl)-2-oxoethyl]acetamide 
• 588-46-5 N-(phenylmethyl)acetamide 
• 100-52-7 benzaldehyde 

Downstream Products

• 13099-80-4 3-benzyl-4-chlorooxalyl-2-methyl-5-oxo-4,5-dihydro-oxazolium betaine 
• 87281-49-0 N-benzyl-3-carbomethoxy-2-methylpyrrole 
• 87281-50-3 methyl 1-benzyl-5-methyl-1H-pyrrole-3-carboxylate 
• 220354-32-5 3-benzyl-4-trifluoroacetyl-2-methyl-1,3-oxazol-3-ium-5-olate 
• 345894-62-4 1-benzyl-4-trifluoromethyl-4-hydroxy-2-methyl-4,5-dihydroimidazole 
• 1426231-11-9 4-benzyl-6-trifluoromethyl-5,6-dihydro-3-methyl-4H-1,2,4-oxadiazin-6-ol 

Relevant academic research and scientific papers

Diversity Oriented Clicking (DOC): Divergent Synthesis of SuFExable Pharmacophores from 2-Substituted-Alkynyl-1-Sulfonyl Fluoride (SASF) Hubs

Diversity Oriented Clicking (DOC) is a unified click-approach for the modular synthesis of lead-like structures through application of the wide family of click transformations. DOC evolved from the concept of achieving “diversity with ease”, by combining classic C?C π-bond click chemistry with recent developments in connective SuFEx-technologies. We showcase 2-Substituted-Alkynyl-1-Sulfonyl Fluorides (SASFs) as a new class of connective hub in concert with a diverse selection of click-cycloaddition processes. Through the selective DOC of SASFs with a range of dipoles and cyclic dienes, we report a diverse click-library of 173 unique functional molecules in minimal synthetic steps. The SuFExable library comprises 10 discrete heterocyclic core structures derived from 1,3- and 1,5-dipoles; while reaction with cyclic dienes yields several three-dimensional bicyclic Diels–Alder adducts. Growing the library to 278 discrete compounds through late-stage modification was made possible through SuFEx click derivatization of the pendant sulfonyl fluoride group in 96 well-plates—demonstrating the versatility of the DOC approach for the rapid synthesis of diverse functional structures. Screening for function against MRSA (USA300) revealed several lead hits with improved activity over methicillin.

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.

A stable, convertible isonitrile as a formic acid carbanion [ -COOH] equivalent and its application in multicomponent reactions

The application of 2-(2,2-dimethoxyethyl) phenyl isonitrile in Ugi, Passerini, and Ugi-Smiles reactions is described. The simple transformation to highly activated indolyl amides allows functional-group conversion of the isonitrile moiety into a variety of carboxylic acid derivatives, overall acting as a neutral, nucleophilic COOH equivalent. Georg Thieme Verlag Stuttgart.

Convenient synthesis of 4-trifluoromethyl-substituted imidazole derivatives

Mesoionic 4-trifluoroacetyl-1,3-oxazolium-5-olates (1), obtained from the reaction of N-acyl-N-alkylglycines (2) with trifluoroacetic anhydride, react with ammonia to give 4-trifluoromethyl-3,4-dihydroimidazoles (3) in high yields. Dehydration of 3 gives

Fast ester cleavage of sterically hindered α- and β-aminoesters under non-aqueous conditions. Application to the kinetic resolution of aziridine esters

Various protected α- and β-aminoesters undergo fast ester cleavage by treatment with t-BuOK in THF. The accelerating effect of a neighboring chelating group was used for the efficient kinetic resolution of non-racemic aziridine esters. (C) 2000 elsevier Science Ltd.

Synthetic Application of Cyanoaminosilanes as Azomethine Ylide Equivalents

A series of α-cyanoaminosilanes have been found to act as azomethine ylide equivalents.Treatment of these compounds with silver fluoride in the presence of electron-dificient alkynes and olefins gives substituted pyrroles and pyrrolidines in high yield.It was found that N-benzyl-N-(cyanomethyl)-N-amine undergoes stereospecific cycloaddition with dimethyl fumarate and maleate.The stereospecificity of the reaction is consistent with a concerted cycloaddition reaction.The cycloaddition behavior of an unsymmetrically substituted α-cyanosilylamine with methyl propiolate was also examined and found to react with high overall regioselectivity.The synthetic utility of cyanoaminosilanes as azomethine ylide equivalents was demonstrated by the preparation of a Reniera isoindole alkaloid.The key step in the synthesis involved the reaction of 2-methyl-3-methoxyquinone with N-methyl-N-(cyanomethyl)-N-amine in the presence of silver fluoride to give 2,5-dimethyl-6-methoxy-2H-isoindole-4,7-dione in good yield.