30438-94-9

Upstream product

• 106-47-8 4-chloro-aniline 
• 106-95-6 allyl bromide 
• 107-18-6 allyl alcohol 
• 3296-05-7 1-azido-4-chlorobenzene 
• 15022-08-9 diallylcarbonate 
• 1121-60-4 pyridine-2-carbaldehyde 

Downstream Products

• 76388-34-6 trans-2,6-dimethyl-4-(4-chlorophenyl)-1-(4-methylphenyl)piperazine 
• 76388-36-8 cis-2,6-dimethyl-1,4-bis(4-chlorophenyl)piperazine 
• 76388-35-7 cis-2,6-dimethyl-4-(4-chlorophenyl)-1-(4-methoxyphenyl)piperazine 
• 76388-35-7 trans-2,6-dimethyl-4-(4-chlorophenyl)-1-(4-methoxyphenyl)piperazine 
• 5044-38-2 1-(4-chlorophenyl)-1H-pyrrole 
• 1118507-33-7 C₁₂H₁₄ClN 
• 28192-10-1 1-(4-chlorophenyl)-2,5-dihydro-1H-pyrrole 
• 1316312-70-5 ethyl allyl-(2-allyl-4-chloro-phenyl)carbamate 
• 1316312-41-0 6-chloro-2-methyl-1-(toluene-4-sulfonyl)-1,2-dihydro-quinoline 
• 1316312-33-0 ethyl 6-chloro-2-methyl-2H-quinoline-1-carboxylate 
• 1316312-22-7 N-(2-buta-1,3-dienyl-4-chloro-phenyl)-2,2,2-trifluoro-acetamide 
• 1316312-21-6 N-(2-buta-1,3-dienyl-4-chloro-phenyl)-acetamide 
• 1316312-20-5 N-(2-buta-1,3-dienyl-4-chloro-phenyl)-benzamide 
• 1316312-19-2 N-(2-buta-1,3-dienyl-4-chlorophenyl)-4-methyl-benzenesulfonamide 

Relevant academic research and scientific papers

Highly efficient Ru(ii)-alkylidene based Hoveyda-Grubbs catalysts for ring-closing metathesis reactions

Three novel phosphine-free Ru-alkylidenes (7a-7c) have been synthesized and utilized as efficient catalysts for ring closing metathesis (RCM) reaction. Spectroscopic data, i.e. NMR and HRMS, along with single crystal X-ray diffraction analysis, were used

Silica-functionalized CuI: An efficient and selective catalyst for N-benzylation, allylation, and alkylation of primary and secondary amines in water

Silica-functionalized CuI has been reported as an efficient and selective catalyst for the selective mono-N- and N,N-dibenzylation, allylation, and alkylation of primary amines with benzylic, allylic, and alkyl halides using NaOH as base in aqueous medium. By changing the reaction temperature, mono- or di-benzylation, allylation, or alkylation could be achieved in good yield and selectivity. Secondary amines have also been benzylated, allylated, and alkylated under similar conditions. SiO2-CuI has been characterized by Fourier transform-infrared, atomic absorption spectrometry, thermalgravimetric analysis, X-ray diffraction, scanning electron microscopy, and transmission electron microscopy, and found to be highly selective and recyclable under the reaction conditions. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.] Copyright

Assisted tandem catalytic RCM-aromatization in the synthesis of pyrroles and furans

An assisted tandem catalytic transformation of diallyl amines and diallyl ethers into N-aryl pyrroles and furans, respectively, is described. The sequence relies on ring closing metathesis followed by dehydrogenation of the initially formed dihydropyrroles and dihydrofurans. Both steps are Ru-catalyzed, but the sequence requires only one precatalyst, because conversion of the metathesis catalyst into the dehydrogenation catalyst is achieved in situ, triggered by the oxidant tert-butyl hydroperoxide.

Sequential combination of ruthenium-, base-, and gold-catalysis - A new approach to the synthesis of medicinally important heterocycles

A general approach to the high-yielding synthesis of medicinally important heterocycles was achieved through the sequential combination of ring-closing metathesis, base-induced ring opening (BIRO), hydroamination, and a Diels-Alder reaction of functionalized allyl-(2-allylphenyl)amines in the presence of a catalytic amount of Grubbs' second-generation catalyst, base (tBuOK), and [AuCl(PPh3)]/AgOTf. Herein, we also demonstrate the important electronic factors in the BIRO of N-substituted-benzo[b]azepines for the regioselective synthesis of functionalized (Z)-N-substituted-2-(buta-1,3-dienyl) phenylamines in very good yields with high purity; these are very good, useful compounds in medicinal chemistry. We also discovered the selective cascade synthesis of privileged hexahydrophenanthridines from (Z)-N-substituted-2-(buta- 1,3-dienyl)phenylamines by gold catalysis in moderate to good yields with >99 % diastereomeric excess. The possible reaction mechanism for the unusual hydroamination followed by [4+2] cycloaddition of functionalized (Z)-N-substituted-2-(buta-1,3-dienyl)phenylamines through gold catalysis is discussed in this work. A novel process for the synthesis of highly substituted, medicinally important heterocycles was achieved through the sequential combination of ring-closing methathesis, base-induced ring opening, hydroamination, and Diels-Alder reaction of functionalized allyl-(2-allylphenyl) amines in the presence of a catalytic amount of [Ru], base, and [Au] (see scheme). Copyright

Palladium-catalyzed cyclization/cyclopropanation reaction for the synthesis of fused N-containing heterocycles

Palladium-catalyzed cyclization/cyclopropanation can be used to convert a range of substituted cyclic N-aryl allyl/methallyl amines efficiently and selectively to the corresponding fused tetrahydropyridine/cyclopropane-fused isoquinoline derivatives via β

Sequential aza-Claisen rearrangement and ring-closing metathesis as a route to 1-benzazepine derivatives

A synthetic strategy based on sequential application of aza-Claisen rearrangement and ring-closing metathesis reaction as key steps has been developed for the synthesis of various 1-benzazepine derivatives of pharmaceutical relevance. Georg Thieme Verlag

Rate acceleration and diastereoselectivity in chelation-controlled indium-promoted Barbier allylation of pyridine-2- and quinoline-2-imines in aqueous solvents

The imines generated in situ from 2-pyridinecarboxaldehyde/2- quinolinecarboxaldehyde and aryl amines undergo indium-mediated Barbier allylation in aqueous media to provide homoallylic amines. Crotyl and cinnamyl bromides lead to diastereoselective allyla

Indium-mediated barbier reactions of azides: A facile synthesis of N-allylamine derivatives

N-Allylic amines are conveniently prepared in high yields by the reaction of azides with allylindium reagents in the presence of sodium iodide in DMF at ambient temperature.

Reaction of primary aromatic amines with alkyl carbonates over NaY faujasite: A convenient and selective access to mono-N-alkyl anilines

At atmospheric pressure and at 130-160°C, primary aromatic amines (p-XC6H4NH2, X = H, Cl, NO2) are mono-N-alkylated in a single step, with symmetrical and asymmetrical dialkyl carbonates [ROCOOR′, R = Me, R′ = MeO(CH2)2O(CH2)2; R = R′ = Et; R = R′ = benzyl; R = R′ = allyl; R = Et, R′ = MeO(CH2)2O(CH2)2], in the presence of a commercially available NaY faujasite. No solvents are required. Mono-N-alkyl anilines are obtained with a very high selectivity (90-97%), in good to excellent yields (68-94%), on a preparative scale. In the presence of triglyme as a solvent, the mono-N-alkyl selectivity is independent of concentration and polarity factors. The reaction probably takes place within the polar zeolite cavities, and through the combined effect of the dual acid-base properties of the catalyst.

Direct palladium-catalyzed selective monoallylation of anilines using allylic alcohols

N-Allylation of anilines using allylic alcohols directly to give monoallylic anilines selectively in high yields has been realized by employing palladium acetate-triphenylphosphine as the catalyst. Palladium-catalyzed one-pot cyclization of 2-aminophenols with 2-butene-1,4-diol leads to 3,4-dihydro-2-vinyl-2H-1,4-benzoxazines. (C) 2000 Elsevier Science Ltd.