15582-97-5

Upstream product

• 1056477-06-5 2-bromocyclohexanone 
• 103896-55-5 N-(1-Phenylvinylimino)triphenylphosphorane 
• 107170-78-5 <(1-phenylvinyl)imino>tributylphosphorane 
• 79379-52-5 1-morpholino-4-phenyl-2-oxa-3-azabicyclo<4.4.0>dec-3-ene 
• 33553-23-0 2-phenacylcyclohexanone 
• 109925-95-3 3-Phenyl-8a-trimethylsilanyloxy-4a,5,6,7,8,8a-hexahydro-4H-benzo[e][1,2]oxazine 
• 86831-05-2 2-phenyl-7a-hydroperoxy-4,5,6,7,7a-pentahydroindolenine 
• 77726-81-9 3a,4,5,6,7,7a-hexahydro-1-(1-phenylvinyl)-7a-(1-pyrrolidinyl)-1H-1,2,3-benzotriazole 
• 82031-71-8 trans-2-(2-phenylethynyl)-1-cyclohexanol 
• 286-20-4 cyclohexane-1,2-epoxide 
• 536-74-3 phenylacetylene 
• 1125-99-1 1-(1-Cyclohexen-1-yl)pyrrolidine 
• 70-11-1 α-bromoacetophenone 
• 6651-36-1 1-(Trimethylsilyloxy)cyclohexene 

Downstream Products

• 86700-08-5 (Z)-9-Phenyl-3,4,5,6-tetrahydro-1H-azonine-2,7-dione 
• 86831-05-2 2-phenyl-7a-hydroperoxy-4,5,6,7,7a-pentahydroindolenine 
• 86831-13-2 3-Phenyl-2-aza-spiro[4.4]non-3-en-1-one 
• 86831-09-6 2-phenyl-7a-hydroxy-4,5,6,7,7a-pentahydroindolenine 

Relevant academic research and scientific papers

Divergent Iron-Catalyzed Coupling of O-Acyloximes with Silyl Enol Ethers

An iron-catalyzed coupling reaction of O-acyloximes and O-benzoyl amidoximes with silyl enol ethers is reported. The protocol provides access to functionalized pyrroles, 1,6-ketonitriles, pyrrolines and imidazolines via carbon-centered radicals generated from an initially formed iminyl radical. The intramolecular cyclization and ring-opening processes of the iminyl radical take place preferentially over reactions that proceed through a 1,3-hydrogen transfer, providing insights into iron-catalyzed reactions with oxime derivatives. The cheap and environmentally friendly iron catalyst, the broad substrate scope and the functional group compatibility make this protocol useful for synthesis of valuable nitrogen-containing products.

Efficient Trapping of 1,2-Cyclohexadienes with 1,3-Dipoles

1,2-Cyclohexadienes are transient intermediates that undergo rapid dimerization and intermolecular trapping with activated olefins and heteroatomic nucleophiles. Fluoride-mediated desilylative elimination of readily accessible 6-silylcyclohexene-1-triflates allows the mild, chemoselective, and functional-group tolerant generation of cyclic allene intermediates, which undergo efficient trapping reactions with stable 1,3-dipoles. The reactions proceed with high levels of both regio- and diastereoselectivity. The reaction of cyclic allenes with azides is accompanied by the facile loss of dinitrogen, resulting in the formation of tetrahydroindoles or polycylic aziridines depending on the azide employed.

2-phenylindole and arylsulphonamide: Novel scaffolds bactericidal against mycobacterium tuberculosis

A cellular activity-based screen on Mycobacterium tuberculosis (Mtb) H37Rv using a focused library from the AstraZeneca corporate collection led to the identification of 2-phenylindoles and arylsulphonamides, novel antimycobacterial scaffolds. Both the series were bactericidal in vitro and in an intracellular macrophage infection model, active against drug sensitive and drug resistant Mtb clinical isolates, and specific to mycobacteria. The scaffolds showed promising structure-activity relationships; compounds with submicromolar cellular potency were identified during the hit to lead exploration. Furthermore, compounds from both scaffolds were tested for inhibition of known target enzymes or pathways of antimycobacterial drugs including InhA, RNA polymerase, DprE1, topoisomerases, protein synthesis, and oxidative-phosphorylation. Compounds did not inhibit any of the targets suggesting the potential of a possible novel mode of action(s). Hence, both scaffolds provide the opportunity to be developed further as leads and tool compounds to uncover novel mechanisms for tuberculosis drug discovery.

General and regioselective synthesis of pyrroles via ruthenium-catalyzed multicomponent reactions

A general and highly regioselective synthesis of pyrroles via ruthenium-catalyzed three-component reactions has been developed. A variety of ketones including less reactive aryl and alkyl substrates were efficiently converted in combination with different

Synthesis of nitrodienes, nitrostyrenes, and nitrobiaryls through palladium-catalyzed couplings of β-nitrovinyl and o-nitroaryl thioethers

A highly efficient, base-free, mild protocol for the palladium-catalyzed, copper-activated desulfitative couplings of vinyl and aryl β- nitrothioethers generates a wide variety of conjugated nitroorganics. Orthogonality to traditional Suzuki-Miyaura coupling is demonstrated, as well as synthetic utility, through reductive Cadogan cyclization, for the formation of indoles, carbazoles, and pyrroles.

Synthesis of 4,5,6,7-tetrahydro-1H-indole derivatives through successive sonogashira coupling/Pd-mediated 5-endo-dig cyclization

A one-pot Sonogashira cross-coupling/5-endo-dig cyclization procedure leading to 2-aryl-4,5,6,7-tetrahydroindoles was developed. This short (only two steps from commercially available compounds) sequence avoids harsh conditions and expensive catalysts. Our procedure is highly tolerant to a range of functional groups (amino, nitro, carboxy, cyano, hydroxy, and bromo). A family of 21 tetrahydroindoles was synthesized on a gram scale in a good to excellent yields, which is indicative of the general character and scalability of this reaction. This methodology allows access to indoles bearing miscellaneous substituents at the C2 position (by variation of ArI) and at the nitrogen atom (by variation of RNH2, including chiral moieties). A one-pot sequence based on Sonogashira cross-coupling/Pd-mediated 5-endo-dig cyclization was developed and applied to the gram-scale synthesis of 2-aryl-4,5,6,7- tetrahydroindoles (21 examples). Copyright

Flow synthesis using gaseous ammonia in a Teflon AF-2400 tube-in-tube reactor: Paal-Knorr pyrrole formation and gas concentration measurement by inline flow titration

Using a simple and accessible Teflon AF-2400 based tube-in-tube reactor, a series of pyrroles were synthesised in flow using the Paal-Knorr reaction of 1,4-diketones with gaseous ammonia. An inline flow titration technique allowed measurement of the ammonia concentration and its relationship to residence time and temperature.

Manganese(III)-catalyzed formal [3+2] annulation of vinyl azides and ?-keto acids for synthesis of pyrroles

Manganese(III)-catalyzed formal [3+2] annnulation of vinyl azides and -keto acids has been developed for the synthesis of substituted NH pyrroles with a wide range of substituents. Georg Thieme Verlag Stuttgart.

An efficient pyrrole synthesis via silaphenylmercuric triflate catalyzed cyclization of homopropargyl azides

A mixture of phenylmercuric acetate and trifluoromethanesulfonic acid or silica gel supported phenylmercuric tri-fluoromethanesulfonate (silaphenyl mercuric triflate) efficiently catalyzed the formation of pyrroles from homopropargyl azide derivatives. The reactions proceed using 20 mol% of the heterogeneous catalyst with yields of isolated pyrroles ranging from 74% to 99%. Georg Thieme Verlag Stuttgart · New York.