109949-64-6

Upstream product

• 106-47-8 4-chloro-aniline 
• 91-13-4 α,α'-dibromo-o-xylene 
• 496-14-0 1,3-dihydroisobenzofuran 
• 119-67-5 o-carboxybenzaldehyde 
• 612-14-6 phthalyl alcohol 
• 13519-75-0 N-ethyl-4-chloro-aniline 

Downstream Products

• 109969-19-9 2-(4-Chloro-phenyl)-2,3-dihydro-1H-isoindole; compound with 2,3,5,6-tetrabromo-[1,4]benzoquinone 
• 109975-15-7 2-(4-Chloro-phenyl)-2,3-dihydro-1H-isoindole; compound with 2,3,5,6-tetrachloro-[1,4]benzoquinone 
• 63539-94-6 2,2'-bis-(4-chloro-phenyl)-[1,1']biisoindolylidene-3,3'-dione 
• 1198-55-6 o-chloranil 
• 37896-11-0 2,3-Dihydro-3-hydroxy-2-(p-chlorophenyl)-1H-isoindol-1-one 
• 7386-21-2 N-(4-chlorophenyl)phthalimide 
• 4775-27-3 2-(4-chlorophenyl)-2,3-dihydro-1H-isoindol-1-one 
• 1262234-87-6 C₂₆H₁₆ClN 

Relevant academic research and scientific papers

Oxidative Desymmetrization of Isoindolines Realized by tert -Butyl Nitrite (TBN) Initiated Radical sp 3C-H Activation Relay (CHAR)

An oxidative desymmetrization of isoindolines was realized by TBN initiated radical sp 3C-H activation relay (CHAR), providing a series of ω-hydroxylactams in high yields. This reaction exhibits broad substrate scope and functional group tolerance, and even N -alkyl iso-indolines can be well tolerated. The mechanistic study shows that the C-H bond oxidation, dioxygen trapping and intramolecular 1,5-H shift might be the key steps to achieve the oxidative desymmetrization.

Practical direct synthesis of: N -aryl-substituted azacycles from N -alkyl protected arylamines using TiCl4and DBU

A novel transformation of N-alkyl protected arylamines and cyclic ethers into N-aryl substituted azacycles is described. Alkyl groups have been used for the protection of amines in organic syntheses. In this synthesis, N-alkyl protected arylamines were reacted with cyclic ethers in the presence of TiCl4 and DBU, crucial reagents affording five- and six-membered azacycles. In particular, utilization of the novel TiCl4/DBU-mediated reaction allows various N-alkyl protected arylamines such as N-methyl-, N-ethyl-, N-isopropyl, and N-tert-butyl arylamines to be readily converted into N-aryl substituted azacycles in high yields. This practical approach using various N-alkyl arylamines leads to the efficient preparation of azacycles.

Synthesis of 2-Arylisoindoline Derivatives Catalyzed by Reusable 1,2,4-Triazole Iridium on Mesoporous Silica through a Cascade Borrowing Hydrogen Strategy

Covalent attachment of a 1,2,4-triazole iridium complex to mesoporous MCM-41 generated a heterogeneous catalyst that was found to be effective in the synthesis of 2-aryl isoindolines, quinolines, cyclic amines, and symmetrical secondary amines through a cascade borrowing hydrogen strategy. Interestingly, the supported heterogeneous iridium catalyst prepared from the 1,2,4-triazole iridium complex and mesoporous MCM-41 exhibited high catalytic activity in the preparation of 2-aryl isoindoline derivatives and symmetrical secondary amines. The catalyst system is highly recyclable for at least five times. Besides the important effect of the triazole, iridium sites grafted on siliceous supports can act as multifunctional catalytic centers and thus greatly enhance the catalytic activity of the catalysts. Furthermore, mechanistic experiments revealed that the reaction is initiated by an initial alcohol dehydrogenation and promoted by an iridium hydride intermediate. Importantly, the direct detection of a diagnostic iridium hydride signal confirmed that the synthesis of 2-aryl isoindolines occurs by a borrowing hydrogen process. This work provides an efficient example of isoindolines synthesis through a borrowing hydrogen strategy.

Iron-Catalysed Switchable Synthesis of Pyrrolidines vs Pyrrolidinones by Reductive Amination of Levulinic Acid Derivatives via Hydrosilylation

A selective production of pyrrolidines vs pyrrolidinones via hydrosilylation of levulinic acid and levulinates by switching of the iron complex catalyst is presented herein. The reactions proceeded efficiently with various anilines and alkylamines under both visible light irradiation and thermal conditions with 43 examples in isolated yields up to 93%. Noticeably, under similar conditions, cyclic amines such as piperidines and azepanes were efficiently synthesized with yields up to 92%, by reaction of anilines with 1,5- or 1,6-keto acids, respectively. Similarly, N-arylinsolidoline compounds can be prepared from 2-formylbenzoic acid in 57–93% yields. (Figure presented.).

Metal-Free Synthesis of N-Aryl-Substituted Azacycles from Cyclic Ethers Using POCl3

A facile method for the synthesis of N-aryl-substituted azacycles from arylamines and cyclic ethers has been developed. In this study, arylamines were treated with cyclic ethers in the presence of POCl3 and DBU to provide five- A nd six-membered azacycles. Using this method, various azacycloalkanes, isoindolines, and tetrahydroisoquinolines were prepared in high yields. This synthetic method offers an efficient approach to the production of azacycles from cyclic ethers.

Synthesis of N-aryl substituted, five- and six-membered azacycles using aluminum-amide complexes

Synthesis of N-aryl substituted, five- and six-membered azacycloalkanes, isoindolines and tetrahydroisoquinolines, has been described. In this synthesis, cyclic ethers (n = 1, 2) were treated with dimethylaluminum-amide reagents, derived from a range of aryl amines and trimethylaluminum, to afford the corresponding azacycles in good yields. This journal is the Partner Organisations 2014.

An efficient method for the synthesis of 2, 3-dihydro-lH-isoindoles

The synthesis of Af-substituted 2, 3-dihydro-lH-isoindoles from α, α'-dibromo-o-xylene and various primary amines in basic medium under ambient conditions is described. Especially the selection of 1, 4-dioxane as solvent and sodium hydroxide as suitable base to maintain the homogeneity of the medium are key steps to promote the reaction efficiently. Primary alkyl amines react faster as compared to their aromatic analogues under the conditions studied. Irrespective of the starting amine used, all the reactions proceed smoothly and provide 2, 3-dihydro-lH-isoindoles derivatives in excellent yields compared to hitherto known methods.

CHARGE-TRANSFER COMPLEXES OF ISOINDOLINES WITH 1,4-BENZOQUINONES

Charge-transfer (CT) complexes of various N-arylisoindolines as donors with 1,4-benzoquinones as ?-acceptors have been studied spectrophotometrically.Effects of substituents