107734-07-6

Upstream product

• 139717-76-3 2-(2-acetoxy-1-isopropylthioethyl)-4-methylaniline 
• 99448-78-9 5-methyl-1-tosylindoline-2,3-dione 
• 98-59-9 p-toluenesulfonyl chloride 
• 608-05-9 5-methyl-indole-2,3-dione 
• 614-96-0 5-methyl-1H-indole 
• 74-88-4 methyl iodide 
• 512-56-1 trimethyl phosphite 
• 80-48-8 methyl p-toluene sulfonate 
• 139717-77-4 2-(1-isopropylthio-2-methoxyethyl)-4-methylaniline 
• 106-49-0 p-toluidine 
• 139717-67-2 N-tosyl-2-(2-acetoxy-1-isopropylthioethyl)-4-methylanilide 
• 139717-68-3 N-topsyl-2-(1-isopropylthio-2-methoxyethyl)-4-methylanilide 

Downstream Products

• 1280136-06-2 ethyl 2-methyl-4-phenyl-4-(5-methyl-1-tosyl-1H-indol-2-yl)but-2(Z)-enoate 
• 1280136-07-3 ethyl 2-methyl-4-phenyl-4-(5-methyl-1-tosyl-1H-indol-2-yl)but-2(E)-enoate 
• 614-96-0 5-methyl-1H-indole 
• 1579269-03-6 5-(4-methoxyphenyl)-9-methyl-2,6-ditosyl-1,2,3,4,5,6-hexahydroazepino[4,3-b]indole 
• 1579268-79-3 N-(3-hydroxy-3-(5-methyl-1-tosyl-1H-indol-2-yl)propyl)-N-(4-methoxybenzyl)-4-methylbenzenesulfonamide 

Relevant academic research and scientific papers

A Catalytic Construction of Indoles via Formation of Ruthenium Vinylidene Species from N-Arylynamides

Treatment of ynamides with a catalytic amount of TpRuCl(PPh3)2 resulted in the construction of indole scaffolds known as privileged structure motifs. This reaction involved a cascade of 1,2-rearrangement and cyclization carrying out C?C bond formation via a ruthenium vinylidene intermediate, as revealed by a deuterium-labeling experiments. Furthermore, the transformation of multi-functionalized ynamide, derived from a practical drug molecule, showed a high functional group tolerance of this reaction. (Figure presented.).

A Series of 2-((1-Phenyl-1H-imidazol-5-yl)methyl)-1H-indoles as Indoleamine 2,3-Dioxygenase 1 (IDO1) Inhibitors

Indoleamine 2,3-dioxygenase 1 (IDO1) is a promising therapeutic target in cancer immunotherapy and neurological disease. Thus, searching for highly active inhibitors for use in human cancers is now a focus of widespread research and development efforts. I

Design, Synthesis, and Antifungal Evaluation of Cryptolepine Derivatives against Phytopathogenic Fungi

Inspired by the widely antiphytopathogenic application of diversified derivatives from natural sources, cryptolepine and its derivatives were subsequently designed, synthesized, and evaluated for their antifungal activities against four agriculturally important fungi Rhizoctonia solani, Botrytis cinerea, Fusarium graminearum, and Sclerotinia sclerotiorum. The results obtained from in vitro assay indicated that compounds a1-a24 showed great fungicidal property against B. cinerea (EC50 4 μg/mL); especially, a3 presented significantly prominent inhibitory activity with an EC50 of 0.027 μg/mL. In the pursuit of further expanding the antifungal spectrum of cryptolepine, ring-opened compound f1 produced better activity with an EC50 of 3.632 μg/mL against R. solani and an EC50 of 5.599 μg/mL against F. graminearum. Furthermore, a3 was selected to be a candidate to investigate its preliminary antifungal mechanism to B. cinerea, revealing that not only spore germination was effectively inhibited and the normal physiological structure of mycelium was severely undermined but also detrimental reactive oxygen was obviously accumulated and the normal function of the nucleus was fairly disordered. Besides, in vivo curative experiment against B. cinerea found that the therapeutic action of a3 was comparable to that of the positive control azoxystrobin. These results suggested that compound a3 could be regarded as a novel and promising agent against B. cinerea for its valuable potency.

Silver-Catalyzed Asymmetric Dearomatization of Electron-Deficient Heteroarenes via Interrupted Barton–Zard Reaction

Herein we report a catalytic asymmetric dearomatization reaction of electron-deficient heteroarenes with α-substituted isocyanoacetates through an interrupted Barton–Zard reaction. A range of optically active pyrrolo[3,4-b]indole derivatives was obtained

B(C6F5)3-Catalyzed Highly Chemoselective Reduction of Isatins: Synthesis of Indolin-3-ones and Indolines

A chemo- and site-selective reduction reaction of isatin derivatives using catalyst B(C6F5)3 and hydrosilanes is described. This transformation is operationally simple, proceeds under mild conditions, and is resistant to various functional groups. Thus, this efficient reaction using a combination of B(C6F5)3 and BnMe2SiH or B(C6F5)3 and Et2SiH2 could potentially be utilized to produce various indolin-3-ones and indolines, without the need for multistep procedures and metal catalysis conditions.

Iodine-Mediated Electrochemical C(sp2)-H Amination: Switchable Synthesis of Indolines and Indoles

A metal-free electrochemical intramolecular C(sp2)-H amination using iodine as a mediator was developed. This method enables a switchable synthesis of indoline and indole derivatives, respectively, from easily available 2-vinyl anilines.

Electron Transfer Photoredox Catalysis: Development of a Photoactivated Reductive Desulfonylation of an Aza-Heteroaromatic Ring

Herein, we report a protocol for desulfonylation of aza-heteroaromatic rings via photoinduced electron transfer and hydrogen atom transfer. This general protocol has a wide substrate range and moderate to good yields. The utility of the method was demonstrated by the chemoselective desulfonylation of a molecule containing both an aliphatic and an aromatic sulfonamide. (Figure presented.).

Palladium-Catalyzed Methylation of Aryl, Heteroaryl, and Vinyl Boronate Esters

A method for the direct methylation of aryl, heteroaryl, and vinyl boronate esters is reported, involving the reaction of iodomethane with aryl-, heteroaryl-, and vinylboronate esters catalyzed by palladium and PtBu2Me. This transformation occurs with a remarkably broad scope and is suitable for late-stage derivatization of biologically active compounds via the boronate esters. The unique capabilities of this method are demonstrated by combining carbon-boron bond-forming reactions with palladium-catalyzed methylation in a tandem transformation.

Trimethylphosphate as a Methylating Agent for Cross Coupling: A Slow-Release Mechanism for the Methylation of Arylboronic Esters

A methyl group on an arene, despite its small size, can have a profound influence on biologically active molecules. Typical methods to form a methylarene involve strong nucleophiles or strong and often toxic electrophiles. We report a strategy for a new, highly efficient, copper and iodide co-catalyzed methylation of aryl- and heteroarylboronic esters with the mild, nontoxic reagent trimethylphosphate, which has not been used previously in coupling reactions. We show that it reacts in all cases tested in yields that are higher than those of analogous copper-catalyzed reactions of MeOTs or MeI. The combination of C-H borylation and this methylation with trimethylphosphate provides a new approach to the functionalization of inert C-H bonds and is illustrated by late-stage methylation of four medicinally active compounds. In addition, reaction on a 200 mmol scale demonstrates reliability of this method. Mechanistic studies show that the reaction occurs by a slow release of methyl iodide by reaction of PO(OMe)3 with iodide catalyst, rather than the typical direct oxidative addition to a metal center. The low concentration of the reactive electrophile enables selective reaction with an arylcopper intermediate, rather than nucleophilic groups on the arylboronate, and binding of tert-butoxide to the boronate inhibits reaction of the electrophile with the tert-butoxide activator to form methyl ether.

Facile synthesis of indoles by K2CO3catalyzed cyclization reaction of 2-ethynylanilines in water

The cyclization reaction of 2-ethynyl-N-sulfonylanilides proceeded efficiently in water with the presence of a catalytic amount of K2CO3under transition metal-free condition to give indoles in high yields. The recovery and reusabilit