33538-09-9

Usage

Chemical Properties

Yellow solid

InChI:InChI=1/C10H12N2/c1-10(2,3)9-6-8(7-11)4-5-12-9/h4-6H,1-3H3

Upstream product

• 99169-45-6 2-tert-butyl-isonicotinic acid amide 
• 100-48-1 pyridine-4-carbonitrile 
• 38442-51-2 tert-butylmercury chloride 
• 75-98-9 Trimethylacetic acid 
• 100616-09-9 6-tert-butyl-3-cyano-2-hydroxy-isonicotinic acid ethyl ester 
• 13395-36-3 ethyl trimethylacetopyruvate 
• 630-19-3 pivalaldehyde 
• 84380-38-1 S-tert-butyl O-ethyl carbonodithioate 
• 20859-02-3 L-tert-Leucine 
• 100129-69-9 methyl 2-tert-butyl-6-chloroisonicotinate 
• 102015-02-1 2-tert-butyl-6-hydroxy-isonicotinic acid 
• 117653-87-9 2-tert-butyl-isonicotinic acid methyl ester 
• 35448-10-3 oxalic acid mono-tert-butyl ester 

Downstream Products

• 91940-84-0 2-(tert-butyl)isonicotinic acid 

Relevant academic research and scientific papers

Mn(II)-catalyzed C-H alkylation of imidazopyridines and N-heteroarenes via decarbonylative and cross-dehydrogenative coupling

A Mn(II)-catalyzed efficient C-H alkylation of imidazoheterocycles and N-heteroarenes with aliphatic aldehydes has been developed via oxidative decarbonylation. Other alkylating agents such as cyclic alkanes, ethers, and alcohols also coupled with N-heteroarenes through cross-dehydrogenative coupling. Regioselectively C5-alkylated imidazoheterocycles were synthesized in good yields. Experimental results show that radical pathway might be involved in this reaction.

Xanthate-Mediated Incorporation of Quaternary Centers into Heteroarenes

The xanthate-mediated addition of tertiary alkyl radicals to heteroarenes enabled the easy functionalization of heteroaromatic rings as well as more decorated structures, such as marketed drugs or agrochemicals. This work provides a synthetic tool for efficiently exploring the chemical space by allowing late-stage diversification with a high tolerance toward functional groups.

Unprotected Amino Acids as Stable Radical Precursors for Heterocycle C-H Functionalization

An efficient and general method for the C-H alkylation of heteroarenes using unprotected amino acids as stable alkyl radical precursors is reported. This one-pot procedure is performed open to air under aqueous conditions and is effective for several natural and unnatural amino acids. Heterocycles of varying structure are suitably functionalized, and reactivity trends reflect the nucleophilic character of the radical species generated.

PROTEOMIMETIC COMPOUNDS AS INHIBITORS OF THE INTERACTION OF A NUCLEAR RECEPTOR WITH COACTIVATOR PEPTIDES

The present invention relates to compounds, pharmaceutical compositions and methods which inhibit the binding of coactivator proteins in nuclear receptors, including estrogen receptors (alpha and/or beta), androgen receptors, thyroid receptors and peroxis

Helix mimetics as inhibitors of the interaction of the estrogen receptor with coactivator peptides

The short and curlies: A new α-helix mimetic based on a pyridylpyridone scaffold has been developed to bind to the estrogen receptor (ER) by mimicking the key leucine side chains of coactivator LXXLL boxes (L= leucine, X = any amino acid). These inhibitor

Acid- or base-promoted photostimulated homolytic tert-butylation of pyridines and thiophenes

Regioselective photostimulated homolytic tert-butylations for heteroaromatics such as pyridines or thiophenes are investigated with tert-butylmercury(II) chloride in the presence of toluene-p-sulfonic acid (PTSA) or 1,4-diaza-bicyclo[2.2.2]octane (DABCO)

A Novel, Simple and Cheap Source of Alkyl Radicals from Alcohols, Useful for Heterocyclic Substitution

Alkyl radicals were easily produced from secondary or tertiary alcohols in a cheap and simple way by silver-catalyzed decarboxylation of oxalic acid monoesters by S2O8(2-).They were utilized for the alkylation of heteroaromatic bases in a two-phase system, with high yields and selectivity.

Homolytic alkylation of heteroaromatic bases : The problem of monoalkylation

The silver-catalyzed decarboxylation of carboxylic acids by persulphate leads to alkyl radicals, which have been utilized for the selective alkylation of heteroaromatic bases. The method is particularly efficient in a water-chlorobenzene two-phase system for two reasons : it considerably increases the selectivity in monoalkylation when more positions of high nucleophilic reactivity (i.e. α and γ) are available in the heterocyclic ring (i.e. quinoline , 4-cyano- and 4-ethylpyridine, pyrazine , quinoxaline etc.) and it determines a much higher efficiency for the radical sources when the silver salt catalysis is deactivated by complexation of the salt with the heterocyclic compound . The high selectivity in monoalkylation has been obtained by the combination of polar effects and the increased lipophilicity of the alkylated product, which makes its extraction from the aqueous solution by the organic solvent easier.

Nucleophilic Character of the Alkyl Radicals. 19. Absolute Rate Constants in the Homolytic Alkylation of Protonated Heteroaromatic Bases by n-Butyl and tert-Butyl Radicals

The rate constants for the homolytic alkylation of protonated heteroaromatic bases (quinoline, pyridine, and 4-cyano-, 4-acetyl-, 4-methyl-, and 4-methoxypyridine) by n-butyl and tert-butyl radicals were measured at 57 deg C by competition of the aromatic addition with the alkyl radical oxidation by Cu2+ salts (for which the rates are known).With the more activated substrates (quinoline and 4-cyano- and 4-acetylpyridine) the tert-butyl radical is significantly more reactive then the n-butyl radical, clearly showing that polar effects are more important than steric and enthalpic effects in determining the reaction rates.The reversibility of the alkylation by the tert-butyl radical is discussed.