602262-03-3

Upstream product

• 4210-32-6 4-tert-butyl benzonitrile 
• 180261-48-7 4-tert-butyl benzene carbaldehyde oxime 
• 667-27-6 Ethyl bromodifluoroacetate 
• 769-92-6 4-tert-Butylaniline 
• 63429-97-0 N-(4-(tert-butyl)phenyl)formamide 

Downstream Products

• 20330-45-4 4-tert-butylacetanilide 
• 1357486-35-1 C₁₄H₂₀N₂O 
• 803729-70-6 C₁₃H₁₈N₂O 

Relevant academic research and scientific papers

Anodic Oxidation of Aminotetrazoles: A Mild and Safe Route to Isocyanides

A new electrochemical method for the preparation of isocyanides from easily accessible aminotetrazole derivatives has been developed, which tolerates an unprecedented range of functional groups. The use of chemical, rather than electrochemical, oxidation to afford isocyanides was also demonstrated, which provides access to these compounds for those without electrosynthesis equipment. The practicality of scale-up using flow electrochemistry has been demonstrated, in addition to the possibility of using electrochemically generated isocyanides in further reactions.

Synthesis of β-Aminoenones via Cross-Coupling of In-Situ-Generated Isocyanides with 1,3-Dicarbonyl Compounds

An efficient and practical strategy for the synthesis of β-aminoenones from a three-component reaction was developed. Ethyl bromodifluoroacetate serves as a C1 source in this strategy, forming isocyanides in situ with primary amines. This reaction represents the first example of utilization of readily available starting materials to generate isocyanides in situ and sequentially fully converted to β-aminoenones, avoiding the generation of byproduct imines and overinsertion products. The mechanism study suggested that this method involves activation of two C(sp3)-F bonds and the formation of isocyanides, which might nourish both isocyanide chemistry and fluorine chemistry.

Radical perfluoroalkylation - Easy access to 2-perfluoroalkylindol-3-imines-via electron catalysis

Arylisonitriles (2 equivalents) react with alkyl and perfluoroalkyl radicals to form 2-alkylated indole-3-imines via two sequential additions to the isonitrile moiety followed by homolytic aromatic substitution. The three component reaction comprises three C-C bond formations. The endocyclic imine functionality in the products is more reactive in follow up chemistry and hydrolysis of the exocyclic imine leads to 3-oxindoles that show fluorescence properties.

Isocyanides as influenza A virus subtype H5N1 wild-type M2 channel inhibitors

Basic bulky amines such as amantadine are well-characterized M2 channel blockers, useful for treating influenza. Herein we report our surprising findings that charge-neutral, bulky isocyanides exhibit activities similar to - or even higher than - that of amantadine. We also demonstrate that these isocyanides have potent growth inhibitory activity against the H5N1 virus. The -NH2 to -N≡C group replacement within current anti-influenza drugs was found to give compounds with high activities at low-micromolar concentrations. For example, a tenfold improvement in potency was observed for 1-isocyanoadamantane (27), with an EC50 value of 0.487 μm against amantadine-sensitive H5N1 virus as determined by both MTT and plaque-reduction assays, without showing cytotoxicity. Furthermore, the isocyanide analogues synthesized in this study did not inhibit the V27A or S31N mutant M2 ion channels, according to electrophysiology experiments, and did not exhibit activity against amantadine-resistant virus strains. Charge-neutral bulky isocyanides were found to exhibit antiviral activities similar to - or even higher than - that of amantadine. Moreover, we demonstrated that these isocyanides have potent growth inhibitory activity against the wild-type H5N1 virus. The NH2 to N≡C group replacement within current anti-influenza drugs was found to result in compounds with low-micromolar activities.