36648-40-5

Upstream product

• 64-17-5 ethanol 
• 32119-56-5 2-(ethyl(phenyl)amino)-1-phenylethan-1-one 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 54470-44-9 1-(3-phenyl-1H-indol-1-yl)ethan-1-one 
• 103-69-5 N-ethyl-N-phenylamine 
• 532-27-4 1-chloroacetophenone 
• 54813-77-3 N-ethyl-N-isopropylaniline 
• 70-11-1 α-bromoacetophenone 
• 5558-66-7 2,2-diphenylpropanoic acid 
• 862487-14-7 (1-isocyanatoethane-1,1-diyl)dibenzene 
• 100-52-7 benzaldehyde 
• 5153-67-3 nitrostyrene 
• 591-50-4 iodobenzene 
• 71-91-0 tetraethylammonium bromide 

Relevant academic research and scientific papers

Synthesis of topologically constrained naphthalimide appended palladium(ii)-N-heterocyclic carbene complexes-insights into additive controlled product selectivity

Topologically constrained naphthalimide appended Pd-NHCs were synthesized and characterized. These structurally related complexes were catalytically compared with previously synthesized Pd-NHCs in the regioselective heteroannulation of o-haloanilines and

Divergent Functionalization of N-Alkyl-2-alkenylanilines: Efficient Synthesis of Substituted Indoles and Quinolines

An efficient divergent functionalization of N-alkylated ortho-alkenylanilines to substituted indoles and quinolines has been accomplished by employing rhodium-catalyzed cross-dehydrogenative coupling and silver-mediated oxidative cyclization, respectively. The developed methods tolerate various functional groups and allow the synthesis of substituted indoles and quinolines in good to excellent yield. Synthetic utility is demonstrated through conversion to an indole with antimicrobial activity and C?H bond functionalization of 2-arylquinolines. Furthermore, a plausible mechanism was proposed based on preliminary mechanistic investigations.

Electronic effect of substituents on anilines favors 1,4-addition to: Trans -β-nitrostyrenes: Access to N -substituted 3-arylindoles and 3-arylindoles

A simple and an efficient method for the regioselective synthesis of N-alkyl/aryl/H 3-arylindole derivatives from N-substituted anilines and trans-β-nitrostyrenes has been described using 10 mol% of bismuth(iii) triflate as a catalyst in acetonitrile at 80 °C. The present protocol profits from the formation of new C-C and C-N bonds, broad substrate scope and moderate to good yields.

A Copper-Catalyzed Aerobic [1,3]-Nitrogen Shift through Nitrogen-Radical 4-exo-trig Cyclization

A novel radical [1,3]-nitrogen shift catalyzed by copper diacetate under an oxygen atmosphere (1 atm) has been developed for the construction of a diverse range of indole derivatives from α,α-disubstituted benzylamine. In this reaction, oxygen was used as a clean terminal oxidant, and water was produced as the only by-product. Five inert bonds were cleaved, and two C?N bonds and one C?C double bond were constructed in one pot during this transformation. This unique method demonstrated broad application protential for the late-stage modification of biologically active natural products and drugs. Mechanistic investigations indicate that a unique 4-exo-trig cyclization of an aminyl radical onto a phenyl ring is involved in the catalytic cycle.

Cobalt(III)-Catalyzed Intramolecular Cross-Dehydrogenative C?H/X?H Coupling: Efficient Synthesis of Indoles and Benzofurans

An efficient cobalt(III)-catalyzed intramolecular cross-dehydrogenative C?H/N?H coupling of ortho-alkenylanilines has been developed utilizing O2as a terminal oxidant. The developed reaction tolerates various reactive functional groups and allo

Regiochemistry of the microwave-assisted reaction between aromatic amines and α-bromoketones to yield substituted 1H-indoles

The scope and regioselectivity of the Bischler (or Bischler-Moehlau) reaction between aromatic amines and α-bromoketones has been studied by computational and experimental techniques. It has been found that in many cases the reaction yields are improved under microwave irradiation and working in the absence of solvent. When di- and trisubstituted amines are used as substrates the regioselectivity of the reaction is different to that obtained with the corresponding primary anilines. The reaction between benzene-1,2-diamine and α-bromoacetophenones under the same conditions yields 2-substituted quinoxalines instead of indoles. Finally, when pyridin-2-amines and pyrimidine-2-amines are allowed to react with the corresponding α-bromoacetophenones, the corresponding imidazo[1,2-a]pyridines and imidazo[1,2-a]pyrimidines are obtained, respectively. The Royal Society of Chemistry.

Diborane as reducing agent: Part VII - Novel reduction of indole-1-ketones to 1-alylindoles to 1-alkylindoles and mechanism of reduction of indole-1-aldehydes and ketones

Borane/THF reduction of nine indole-1-ketones (1a-1i) forms 1-ethylindoles (6a-6h) and the 1-benzylindole (6i) in 50-80percent yields.The ketones 1h and 1i, each of which bears phenyl groups at positions 2 and 3, also undergo deacylation to furnish 2,3-diphenylindole (8) in ca. 40percent yield.The mechanism of formation of both 8 and 6a-6i have been rationalised.The rate of borane/THF reduction of 1 is apparently slower than that of indole-1-carboxaldehydes (9).An attempt has been made to throw some light on the cause of this difference.

Cyclisation indolique selon Bischler en presence d'acides de Lewis

In a comparative study of various catalysts (hydrochloric acid, Lewis acids) in the Bischler cyclization of α-aminoketones to indoles, aluminium chloride appears as the most active catalyst.Isomerization of β to α-indoles can be observed by raising the reaction temperature.The mechanism seems different from the one frequently suggested by most authors, since it does not affect intermediate aminoketones but indoles.