87587-24-4

Upstream product

• 87587-23-3 N-benzyl-N-phenyl-O-(trimethylsilyl)hydroxylamine 
• 693-02-7 hex-1-yne 
• 15111-14-5 2-iodo-N-(phenylmethylene)-benzenamine 
• 615-43-0 2-iodophenylamine 
• 3844-94-8 1-(trimethylsilyl)-1-hexyne 
• 76464-99-8 N-benzyl-2-iodoaniline 
• 100-52-7 benzaldehyde 
• 116491-50-0 2-(hex-1-ynyl)aniline 

Downstream Products

• 1380395-23-2 methyl 1-benzyl-2-butyl-1H-indole-3-carboxylate 
• 1615653-08-1 N-benzyl-N-{2-(1-hexyn-1-yl)phenyl}-2-oxo-2-phenylacetamide 
• 1615653-20-7 N-benzyl-2-diethoxyphosphoryloxy-N-{2-(1-hexyn-1-yl)phenyl}-2-phenylacetamide 
• 1432733-30-6 1-benzyl-3-butyl-4-chloroquinolin-2(1H)-one 
• 1246955-89-4 C₁₉H₂₃NO 
• 1246955-88-3 2-(3-butyl-2-phenylquinolin-4-yl)-N-(phenylmethyl)aniline 

Relevant academic research and scientific papers

Indazole 2-oxides compound and method for preparing indazole 2-oxides compound for providing a nitrogen heterocyclic compound used as a precursor for drugs

Provided is a method for preparing an indazole 2-oxides compound, which comprises the step of: performing a cyclization reaction on 2-alkynyl aniline compound and tert-butylnitrite represented by formula (1) in the presence of bis(dibenzylideneacetone) palladium so as to produce an indazole 2-oxides compound, in which, in the formulae (1) and (2), R1 , R2 , R3 and R4 are each hydrogen, halogen or alkyl group; X1 represents an alkyl group, a first chemical structure, a second chemical structure or a third chemical structure where T1 , T2 , T3 , T4 and T5 are each hydrogen, halogen, alkoxy group, or alkyl group; X2 represents hydrogen, cycloalkyl group, alkyl group, alkenyl group, thienyl group, unsubstituted phenyl group, or substituted phenyl group, where the substituent is selected from the group consisting of an alkyl group, an alkoxy group, a halogen, a haloalkyl group, -CN, or -NO2.

Bis(dibenzylideneacetone)palladium(0)/tert-Butyl Nitrite- Catalyzed Cyclization of o-Alkynylanilines with tert-Butyl Nitrite: Synthesis and Applications of Indazole 2-Oxides

An efficient method for the synthesis of 1-benzyl/arylindazole 2-oxides via a bis(dibenzylideneacetone)palladium(0) [Pd(dba)2]/tert-butyl nitrite (TBN)-catalyzed reaction of o-alkynylaniline derivatives with TBN is reported. The overall transfo

Borane-catalyzed indole synthesis through intramolecular hydroamination

The reaction of 2-alkynyl anilines with catalytic amounts of B(C6F5)3 (5 mol%) resulted in the formation of 2-substituted indoles according to an intramolecular hydroamination in good to excellent yields. Reaction intermediates as well as products were characterized by NMR spectroscopy and by X-ray crystallography. The domino hydroamination/hydrogenation sequence allowed the efficient synthesis of tetrahydroquinoline 8 in good yield.

Simple and Mild Synthesis of Indoles via Hydroamination Reaction Catalysed by NHC-Gold Complexes: Looking for Optimized Conditions

An efficient heterocyclization of 2-alkynylanilines to indole derivatives has been developed. The reaction proceeds under very mild conditions using small amounts of a gold precatalyst. A range of substrates possessing various functional groups were employed, and the substituted indoles were obtained in very good yields.

Stereoselective Synthesis of Methylene Oxindoles via Palladium(II)-Catalyzed Intramolecular Cross-Coupling of Carbamoyl Chlorides

We report a highly robust, general and stereoselective method for the synthesis of 3-(chloromethylene)oxindoles from alkyne-tethered carbamoyl chlorides using PdCl2(PhCN)2 as the catalyst. The transformation involves a stereo- and regioselective chloropalladation of an internal alkyne to generate a nucleophilic vinyl PdII species, which then undergoes an intramolecular cross-coupling with a carbamoyl chloride. The reaction proceeds under mild conditions, is insensitive to the presence of moisture and air, and is readily scalable. The products obtained from this reaction are formed with >95:5 Z:E selectivity in nearly all cases and can be used to access biologically relevant oxindole cores. Through combined experimental and computational studies, we provide insight into stereo- and regioselectivity of the chloropalladation step, as well as the mechanism for the C-C bond forming process. Calculations provide support for a mechanism involving oxidative addition into the carbamoyl chloride bond to generate a high valent PdIV species, which then undergoes facile C-C reductive elimination to form the final product. Overall, the transformation constitutes a formal PdII-catalyzed intramolecular alkyne chlorocarbamoylation reaction.

Intramolecular cyclization of alkynyl α-ketoanilide utilizing [1,2]-phospha-brook rearrangement catalyzed by phosphazene base

A novel catalytic cyclization reaction of alkynyl α-ketoanilide was developed by utilizing the [1,2]-phospha-Brook rearrangement. This reaction involves the generation of an amide enolate via the umpolung process, that is the addition of dialkyl phosphite to a keto moiety followed by the [1,2]-phospha-Brook rearrangement, and the subsequent intramolecular addition of the enolate to an alkyne to afford 3,4-dihydro-2-quinolone derivatives. Under high-temperature reaction conditions, further rearrangement of the allylic phosphate moiety occurs to provide 2-quinolone derivatives.

A general synthesis of indole-3-carboxylic esters by palladium-catalyzed direct oxidative carbonylation of 2-alkynylaniline derivatives

A general synthesis of indole-3-carboxylic esters by direct Pd-catalyzed oxidative carbonylation of readily available 2-alkynylaniline derivatives is reported. In particular, 2-alkynylanilines bearing an internal triple bond and a secondary amino group (1) were directly converted into indole-3-carboxylic esters 2 in fair to good yields (50-84%) when let to react with CO, O 2, and an alcohol in the presence of the PdI2/KI catalytic system, under relatively mild conditions [100 °C and 20 atm (at 25 °C) of a 4:1 mixture CO/air]. On the other hand, under similar conditions, but in the presence of HC(OMe)3, 2-alkynylanilines bearing an internal triple bond and a primary amino group (7) afforded 1-(dimethoxymethyl)indole-3- carboxylic esters 9 through the intermediate formation of N-(dimethoxymethyl)-2- alkynylaniline derivatives II. Compounds 9 could be conveniently converted into N-unsubstituted indole-3-carboxylic esters 10 by a simple acidic treatment carried out in MeOH/H2O at 80 °C.

A general synthesis of indole-3-carboxylic esters by palladium-catalyzed direct oxidative carbonylation of 2-alkynylaniline derivatives

A general synthesis of indole-3-carboxylic esters by direct Pd-catalyzed oxidative carbonylation of readily available 2-alkynylaniline derivatives is reported. In particular, 2-alkynylanilines bearing an internal triple bond and a secondary amino group (1) were directly converted into indole-3-carboxylic esters 2 in fair to good yields (50-84%) when let to react with CO, O 2, and an alcohol in the presence of the PdI2/ KI catalytic system, under relatively mild conditions [100 °C and 20 atm (at 25 °C) of a 4:1 mixture CO/air]. On the other hand, under similar conditions, but in the presence of HC(OMe)3, 2-alkynylanilines bearing an internal triple bond and a primary amino group (7) afforded 1-(dimethoxymethyl) indole-3-carboxylic esters 9 through the intermediate formation of N-(dimethoxymethyl)-2-alkynylaniline derivatives II. Compounds 9 could be conveniently converted into Nunsubstituted indole-3-carboxylic esters 10 by a simple acidic treatment carried out in MeOH/H2O at 80 °C.

Simple indole synthesis by one-pot sonogashira coupling-NaOH-mediated cyclization

Coupling of o-iodoanilines with terminal alkynes under standard Sonogashira conditions, and further treatment with NaOH under conventional heating or microwave irradiation, afford 2-substituted indoles in usually high yields. Functionalities such as halides, nitro, and cyano groups are tolerated under the reaction conditions. Georg Thieme Verlag Stuttgart.

2,3-Disubstituted benzofuran and indole by copper-mediated C-C bond extension reaction of 3-zinciobenzoheterole

A metalative 5-endo-dig cyclization reaction of 2-ynylphenoles or anilines effected by BuLi and ZnCl2 produces 3-zinciobenzoheteroles in excellent yield. These intermediates have been transmetalated to the corresponding cuprates and allowed to react with electrophiles to produce a variety of 2,3-disubstituted benzofurans and indoles.