490035-95-5

Upstream product

• 15833-00-8 o-aminophenyldimethylcarbinol 
• 134-20-3 2-carbomethoxyaniline 
• 52562-19-3 2-isopropenylaniline 
• 100-52-7 benzaldehyde 
• 551-93-9 2-aminoacetophenone 
• 100-39-0 benzyl bromide 
• 118-92-3 anthranilic acid 
• 55369-69-2 2-(benzylamino)benzoic acid methyl ester 
• 106899-21-2 2-(benzylamino)-α,α-dimethylbenzyl alcohol 
• 110674-68-5 1-phenyl-N-(2-(prop-1-en-2-yl)phenyl)methanimine 

Downstream Products

• 53551-99-8 1-benzyl-4-methylquinolin-2(1H)-one 
• 1448670-20-9 5-methyl-11-phenylisoindolo[2,1-a]quinoline-7,10-dione 
• 1448670-30-1 5-methyl-13-phenylbenzo[5,6]isoindolo[2,1-a]quinoline-7,12-dione 
• 1610556-28-9 C₁₇H₁₆INO 
• 17017-58-2 1-benzyl-3-methyl-1H-indole 
• 52562-19-3 2-isopropenylaniline 
• 4789-76-8 4-methyl-2-phenylquinoline 
• 114081-14-0 1-benzyl-3,3-dimethyl-1,3-dihydro-indol-2-one 
• 902776-66-3 N-benzyl-N-[2-(prop-1-en-2-yl)phenyl]-1-cyanoformamide 
• 402822-97-3 1-benzyl-4-methyl-1,2-dihydro-quinoline 

Relevant academic research and scientific papers

Palladium-Catalyzed Carbamoyl-Carbamoylation/ Carboxylation/Thioesterification of Alkene-Tethered Carbamoyl Chlorides Using Mo(CO)6 as the Carbonyl Source

We reported a palladium-catalyzed carbamoyl-carbamoylation/carboxylation/thioesterification of alkene-tethered carbamoyl chlorides using Mo(CO)6 as the carbonyl source. The reactions were typically performed with good functional group compatibility and tolerated different nucleophiles (amines, alcohols, phenols, thiols and water), which provided a new access to amidated/esterificated/thioesterificated/carboxylated oxindoles or lactams bearing an all-carbon quaternary stereocenter under CO gas-free conditions. Furthermore, natural product mutation and divergent late-stage derivatization are the important practical features.

Ir(iii)-Catalysed electrooxidative intramolecular dehydrogenative C-H/N-H coupling for the synthesis of N-H indoles

Herein, an iridium(iii)-catalysed electrooxidative intramolecular dehydrogenative C-H/N-H coupling of unprotected 2-alkenyl anilines is described. The developed method allows the synthesis of a variety of 3-substituted N-H indole scaffolds under undivided electrolytic conditions. Mechanistic studies suggest that the reaction proceeds through the electro-oxidation induced reductive elimination pathway.

Carbocatalytic Cascade Synthesis of Polysubstituted Quinolines from Aldehydes and 2-Vinyl Anilines

Oxidized active carbon (oAC) catalyses the formation of polysubstituted quinolines from o-vinyl anilines and aldehydes. The reaction proceeds in a cascade manner through condensation, electrocyclization and dehydrogenation, and gives access to a wide range of quinolines with alkyl and/or aryl substituents as demonstrated with 40 examples. The metal-free catalytic procedure allows a heterogeneous protocol for the synthesis of various polysubstituted quinolines. The mechanistic studies imply that both the acid and quinoidic groups in oAC are integral for the catalytic manifold. (Figure presented.).

Palladium-Catalyzed Phosphoryl-Carbamoylation of Alkenes: Construction of Nonbenzylic C(sp3)?P(O)R2 Bonds via C(sp3)?Pd(II)?P(O)R2 Reductive Elimination

We report the first example of palladium-catalyzed phosphoryl-carbamoylation of alkene-tethered carbamoyl chlorides with P(O)H compounds. Both H-phosphinates and secondary phosphine oxides are compatible with this reaction. DPE-Phos was used as ligand to facilitate nonbenzylic C(sp3)?P bonds formations via C(sp3)?Pd(II)?P reductive elimination. By using this protocol, a range of phosphorylated oxindoles and lactams were obtained in moderate to good yields. (Figure presented.).

Chemoselectivity for Alkene Cleavage by Palladium-Catalyzed Intramolecular Diazo Group Transfer from Azide to Alkene

Alkenes can be cleaved by means of the (3+2) cycloaddition and subsequent cycloreversion of 1,3-dipoles, classically ozone (O3), but the azide (R?N3) variant is rare. Chemoselectivity for these azide to alkene diazo group transfers (DGT) is typically disfavored, thus limiting their synthetic utility. Herein, this work discloses a palladium-catalyzed intramolecular azide to alkene DGT, which grants chemoselectivity over competing aziridination. The data support a catalytic cycloreversion mechanism distinct from other known metal-catalyzed azide/alkene reactions: nitrenoid/metalloradical and (3+2) cycloadditions. Kinetics experiments reveal an unusual mechanistic profile in which the catalyst is not operative during the rate-controlling step, rather, it is active during the product-determining step. Catalytic DGT was used to synthesize N-heterocyclic quinazolinones, a medicinally relevant structural core. We also report on the competing aziridination and subsequent ring expansion to another N-heterocyclic core structure of interest, benzodiazepinones.

Synthesis of substituted γ-lactam via Pd(0)-catalyzed cyclization of alkene-tethered carbamoyl chloride

Pd(0)-catalyzed carboiodonation of but-3-enylcarbamic chloride has been developed with NaI as additive, which provides a ready access to substituted γ-lactam bearing an alkyl iodide group. This reaction features alkyl iodide reductive elimination as a key step in catalytic cycle, indicating the crucial role of additive NaI.

One-pot ring-closing metathesis/1,3-dipolar cycloaddition through assisted tandem ruthenium catalysis: Synthesis of a dye with isoindolo[2,1-a]quinoline structure

The one-pot tandem reaction of N-alkyl-N-allyl-2-vinylaniline derivatives with benzo- or naphthoquinones and a ruthenium-alkylidene catalyst leads to isoindolo[2,1-a]quinolines in a variety of colors, which can be altered by exchanging the substituent on the core heterocycle (see scheme). This reaction offers a new synthetic method for π-conjugated small molecules from simple aniline derivatives. Copyright

Palladium catalysed tandem cyclisation-anion capture processes. Part 8 [1]: In situ and preformed organostannanes. Carbamyl chlorides and other starter species

A sequential one-pot process is reported involving in situ, palladium catalysed, formation of a series of tributylstannyl-1,2-carbo and heterocyclic dialkylidene-5-membered rings from the corresponding 1,6-diynes and Bu 3SnH. These substrates a

A novel synthesis of substituted quinolines using ring-closing metathesis (RCM): Its application to the synthesis of key intermediates for anti-malarial agents

A method for synthesizing substituted quinolines using ruthenium-catalyzed ring-closing metathesis as a key step has been developed. Substituted 1,2-dihydroquinolines, 4-silyloxy-1,2-dihydroquinoline and 4-methoxy-1,2- dihydroquinoline, were successfully synthesized in excellent yields via ene-ene metathesis and silyl or alkyl enol ether-ene metathesis, respectively. The synthetic intermediates of the antimalarial agents quinine, chloroquine, and PPMP-quinine hybrid were efficiently synthesized by this methodology.

Novel synthesis of oxindoles from carbamoyl chlorides via palladium catalysed cyclisation-anion capture

The synthesis of 3,3-disubstituted and 3-methyleneox-indoles by palladium(0) catalysed cyclisation of carbamoyl chlorides onto proximate alkene or alkyne groups has been achieved in good yields.