67358-21-8

Upstream product

• 124-38-9 carbon dioxide 
• 767-71-5 N-methyl-2,6-dimethylaniline 
• 156267-16-2 benzyl N-(2,6-dimethylphenyl)carbamate 
• 156267-20-8 benzyl N-(2,6-dimethylphenyl)-N-methylcarbamate 
• 27237-52-1 N-methyl-N-2,6-dimethylphenylcarbamoylchloride 
• 91790-39-5 N,7-dimethylindoline-2,3-dione 
• 1127-59-9 7-methyl-1H-indole-2,3-dione 
• 95-53-4 o-toluidine 
• 1132-03-2 2-(hydroxyimino)-N-(2-methylphenyl)acetamide 
• 611-21-2 N,2-dimethylaniline 
• 87-62-7 2,6-dimethylaniline 
• 13508-78-6 N-methyl-2-methylchloroacetanilide 

Downstream Products

• 156136-68-4 1,7-Dimethyl-1,3-dihydro-indole-2-thione 
• 1027940-61-9 1,7-Dimethyl-2-thioxo-2,3-dihydro-1H-indole-3-carboxylic acid phenylamide 
• 5621-16-9 1,7-dimethyl-1H-indole 

Relevant academic research and scientific papers

Annulation reaction of cyclic pyridinium ylides with: In situ generated azoalkenes for the construction of spirocyclic skeletons

Two new types of cyclic pyridinium ylides were designed and further used in reactions with azoalkenes to access structurally diverse spirocyclic compounds. A range of spiropyrazoline oxindoles could be smoothly obtained in up to 99% yield via a [4 + 1] annulation process with oxindole 3-pyridinium ylides as C1 synthons. Similarly, a series of spiropyrazoline indanones could be prepared with indanone 2-pyridinium ylides as C1 synthons. This work represents the first example of cyclic pyridinium ylides as C1 synthons for the efficient construction of spirocyclic compounds.

Palladium(II)/N-Heterocyclic Carbene Catalyzed One-Pot Sequential α-Arylation/Alkylation: Access to 3,3-Disubstituted Oxindoles

Rationally designed fluorene-based mono- and bimetallic Pd-PEPPSI complexes were synthesized and demonstrated to be effective for the one-pot sequential α-arylation/alkylation of oxindoles. This streamlined approach offers efficient access to functionalized 3,3-disubstituted oxindoles in excellent yields (up to 89%) under mild reaction conditions.

Palladium-catalyzed amidation by chemoselective C(sp3)-H activation: Concise route to oxindoles using a carbamoyl chloride precursor

Quite select: A new strategy was developed for the synthesis of various oxindoles from carbamoyl chlorides. Under the optimum reaction conditions, with Ad2PBu as a ligand, tBuCONHOH as an additive, and a CO atmosphere, selective C(sp3/sup

Synthesis of substituted oxindoles from α-chloroacetanilides via palladium-catalyzed C - H functionalization

A novel method for the synthesis of oxindoles is described. In the presence of catalytic palladium acetate and 2-(di-tert-butylphosphino)biphenyl, α-chloroacetanilides are converted to oxindoles in good to excellent yields with high functional group compatibility using triethylamine as a stoichiometric base. The cyclization is highly regioselective, obviating the need for prefunctionalized arenes. Plausible mechanistic pathways for the reaction are discussed. Copyright

Tyrosine kinase inhibitors. 3. Structure-activity relationships for inhibition of protein tyrosine kinases by nuclear-substituted derivatives of 2,2'-dithiobis(1-methyl-N-phenyl-1H-indole-3-carboxamide)

A series of indole-substituted 2,2'-dithiobis(1-methyl-N-phenyl-1H- indole-3-carboxamides) were prepared and evaluated for their ability to inhibit the tyrosine kinase activity of both the epidermal growth factor receptor (EGFR) and the nonreceptor pp60(v-src) tyrosine kinase. The compounds were synthesized by conversion of appropriate 1-methyloxindoles to 1-methyl-2-indolinethiones with P2S5 followed by subsequent reaction with NaH and phenyl isocyanate and oxidative dimerization of the resulting 2,3- dihydro-N-phenyl-2-thioxo-1H-indole-3-carboxamides. The parent compound and many of the substituted analogues were moderately potent inhibitors of both kinase enzymes, but no clear relationships were seen between substitution on the indole ring and inhibitory activity. While 4-substituted compounds were generally inactive, 5-substituted derivatives with electron-withdrawing groups showed inhibitory activity. However, none of the substituted compounds showed significantly better activity than the unsubstituted parent compound. There was generally a good correlation between activity against the EGFR and pp60(v-src) kinases, but several compounds did show some specificity (>20- fold) of inhibition; 5-Cl and 5-Br derivatives preferentially inhibited pp60(v-src), while the 5-CF3 compound preferentially inhibited EGFR. Selected compounds from the series were found to inhibit the growth of Swiss 3T3 fibroblasts with IC50s in the range 2-25 μM, the most active being 4- substituted derivatives. The compounds inhibited bFGF-mediated protein tyrosine phosphorylation in intact cells more effectively than EGFR- or PDGF- mediated phosphorylation.

LITHIATION ROUTES TO OXINDOLES AND 2-INDOLINETHIONES: PRECURSORS TO 2,2'-DITHIOBISINDOLES WITH TYROSINE KINASE INHIBITORY PROPERTIES

N-Substituted oxindoles and 2-indolinethiones can be prepared by lithiation of carboxyl protected N,2-dimethylanilines followed by quenching with CO2 or CS2 respectively. 2-Indolinethione derivatives are also available via demethylation of 2-methylthioindoles, which are prepared by lithiation of N-substituted indoles and treatment with dimethyl disulfide.