861549-91-9

Upstream product

• 106-38-7 para-bromotoluene 
• 36192-63-9 2-amino-4'-methylbenzophenone 
• 27200-84-6 methyl triphenylphosphonium bromide 
• 5720-05-8 4-methylphenylboronic acid 
• 2065-66-9 methyl-triphenylphosphonium iodide 
• 551-93-9 2-aminoacetophenone 
• 1885-29-6 anthranilic acid nitrile 
• 624-31-7 4-tolyl iodide 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 62-53-3 aniline 
• 766-97-2 4-n-methylphenylacetylene 

Downstream Products

• 861577-12-0 4-(p-tolyl)cinnoline 
• 1322605-55-9 1-{2-[1-(4-methylphenyl)ethenyl]phenyl}-1H-pyrrole 
• 1322605-65-1 9-methyl-9-(4-methylphenyl)-9H-pyrrolo[1,2-a]indole 
• 180781-23-1 2-methyl-4-(4-methylphenyl)quinoline 
• 302357-89-7 4-(p-tolyl)quinoline 

Relevant academic research and scientific papers

Synthesis of 1-Amino-2,2,2-trifluoroalkylphosphonates from Alkene-Tethered Trifluoroacetimidoyl Chlorides

The reaction of alkene-tethered trifluoroacetimidoyl chlorides with trialkyl phosphites furnishes 1-amino-2,2,2-trifluoroalkylphosphonates. The products were generated in moderate to good yields, and the scalability of this process was showcased. Partial hydrolysis of the phosphonate moiety was achieved. The cyclization is proposed to occur via formation of an imidoyl phosphonate intermediate that becomes susceptible to nucleophilic attack at nitrogen through the strong electron-withdrawing groups at the imidoyl carbon.

Photocatalyzed Intramolecular [2+2] Cycloaddition of N-Alkyl-N-(2-(1-arylvinyl)aryl)cinnamamides

N-Alkyl-N-(2-(1-arylvinyl)aryl)cinnamamides are converted into natural product inspired scaffolds via iridium photocatalyzed intramolecular [2+2] photocycloaddition. The protocol has a broad substrate scope, whilst operating under mild reaction conditions. Tethering four components forming a trisubstituted cyclobutane core builds rapidly high molecular complexity. Our approach allows the design and synthesis of a variety of tetrahydrocyclobuta[c]quinolin-3(1H)-ones, in yields ranging between 20–99 %, and with excellent regio- and diastereoselectivity. Moreover, it was demonstrated that the intramolecular [2+2]-cycloaddition of 1,7-enynes—after fragmentation of the cyclobutane ring—leads to enyne-metathesis-like products.

PEG-400 as a carbon synthon: Highly selective synthesis of quinolines and methylquinolines under metal-free conditions

A metal-free, peroxide-free, and efficient procedure for the highly selective synthesis of quinolines and methylquinolines was reported. The main feature of this method was that the same substrate can produce quinolines and methylquinolines, respectively, under different reaction conditions. PEG-400 was used as both a reactant and solvent in this reaction. The utility of the designed procedure was also demonstrated by the derivatization of the products to bioactive compounds. This journal is

Efficient synthesis of SCF3-substituted tryptanthrins by a radical tandem cyclization

Herein, we report a new, efficient and atom-economical strategy for the synthesis of SCF3-substituted tryptanthrin derivatives. These previously unreported derivatives were obtained by means of a radical tandem cyclization. The reaction was triggered by addition of a SCF3 radical to a carbon-carbon double bond and involved the formation of a C(sp3)-SCF3 bond, a C(sp2)-C bond, and a C(sp2)-N bond. This method has mild conditions and a wide range of substrates which is particularly useful for the preparation of substituted indolquinazoline derivatives that widely exist in many natural products, but are not easy to obtain by conventional approaches.

Palladium(ii)-catalyzed vinylic geminal double C-H activation and alkyne annulation reaction: Synthesis of pentafulvenes

The first transition-metal-catalyzed vinylic geminal double C(sp2)-H activation and di-substituted alkyne annulation reaction is reported. This palladium(ii)-catalyzed, amide directed reaction of vinylic compounds with di-substituted alkynes offers an efficient synthetic path to pentafulvenes, which are very important compounds because of their bioactivity and interesting optical properties. A FeCl3-mediated transformation of pentafulvenes to fluorescent cyclopenta[b]quinolines is also developed.

Mn(III)-Mediated Regioselective 6-endo-trig Radical Cyclization of o-Vinylaryl Isocyanides to Access 2-Functionalized Quinolines

A Mn(III)-mediated radical cyclization reaction of o-vinylaryl isocyanides and arylboronic acids or diphenylphosphine oxides to access various 2-functionalized quinolines under mild conditions was developed. With the introduction of radical stabilizing substituents (e. g. aryl and methyl group) on vinyl group, this reaction provides a regiospecific 6-endo-trig radical cyclization of o-vinylaryl isocyanides, giving a number of structurally unique and biologically potential 2-functionalized quinoline derivatives.

Iron-Promoted Construction of Indoles via Intramolecular Oxidative C-N Coupling of 2-Alkenylanilines Using Persulfate

Indole scaffold synthesis relies primarily on oxidative C-H amination of N-protected alkenylanilines for C-N intramolecular cyclization reactions. Herein, for the first time, without N-protection, various readily prepared 2-alkenylanilines were transformed into the desired indole products in good yields by using K 2 S 2 O 8 as oxidant in the presence of catalytic amounts of FeF 2. The K 2 S 2 O 8 /FeF 2 system offers a direct and benign synthetic route to 3-arylindoles and it is applicable to a wide range of substituted indoles including drug intermediates.

Palladium(II)/Lewis acid cocatalyzed oxidative annulation of 2-alkenylanilines and propargylic esters: An access to benzo[ b]azepines

An attractive approach to valuable yet synthetically challenging benzo[b]azepines was established via palladium(II)/Lewis acid cocatalyzed oxidative [5 + 2] annulation of readily available 2-alkenylanilines and propargylic esters. The protocol features mild reaction conditions and good functional group tolerance, constituting an array of benzo[b]azepines in yields of 30-75%.

Catalyst-free and selective trifluoromethylative cyclization of acryloanilides using PhICF3Cl

Trifluoromethylation-triggered cyclization of alkenes provides a useful route to CF3-containing cyclic compounds. Current approaches to generate CF3-based initiators from a CF3 source require a catalyst or an activator. This work describes a catalyst-free protocol to innately produce electrophilic CF3 species from PhICF3Cl for trifluoromethylative cyclization of acryloanilides. A new domino biscyclization of dienes has been developed leading to trifluoroethylated tetrahydroindenoquinolinones with chemo- and stereo-selectivity.

Enantioselective Copper-Catalyzed Borylative Cyclization with Cyclic Imides

An enantioselective borylative cyclization cascade utilizing cyclic imides has been developed. We employ a highly enantioselective borylcupration process that includes a 1,2-addition to a cyclic imide. The products contain a valuable hemiaminal and boronate handle for further elaborations within a congested framework. This work demonstrates the utility of cyclic imides as simple precursors to unlock access to sought-after polycyclic indolines. Futhermore, this report highlights the capability to harness reactive catalytic intermediates to exploit otherwise unreactive functional groups.