72288-78-9

Upstream product

• 941-69-5 N-phenyl-maleimide 
• 1576-87-0 trans-2-pentenal 
• 4727-29-1 phthalanilic acid 
• 4792-30-7 3-methylphthalic acid anhydride 
• 62-53-3 aniline 
• 4389-45-1 3-methylantranilic acid 
• 201230-82-2 carbon monoxide 
• 1608-48-6 3-Methyl-1,2-diiodobenzene 
• 118-90-1 ortho-methylbenzoic acid 
• 103-71-9 phenyl isocyanate 

Downstream Products

• 84839-32-7 1-methyl-anti-7,8-diazabicyclo<2.2.2>oct-5-ene-2,3,7,8-tetracarboxylic acid bis-N-phenylimide 
• 84839-32-7 1-methyl-syn-7,8-diazabicyclo<2.2.2>oct-5-ene-2,3,7-tetracarboxylic acid bis-N-phenylimide 
• 7055-03-0 2-methyl-N-phenylbenzamide 
• 23099-05-0 3-methyl-N-phenylbenzamide 

Relevant academic research and scientific papers

Organocatalyzed Synthesis of Highly Functionalized Phthalimides via Diels-Alder Reaction Employing Two Dienophiles

An efficient and facile protocol for the synthesis of biologically and pharmaceutically important phthalimides is developed by l-proline-catalyzed reaction between two dienophiles of α,β-unsaturated aldehydes and maleimides. The reaction involves an efficient benzannulation that proceeds via a formal [4 + 2] cycloaddition of azadiene intermediates generated in situ from enals and N-substituted maleimides. This protocol provides a variety of functionalized phthalimide derivatives, including a potent COX-2 enzyme inhibitor.

Ru-Catalyzed Selective C-H Bond Hydroxylation of Cyclic Imides

We report on cyclic imides as weak directing groups for selective monohydroxylation reactions using ruthenium catalysis. Whereas acyclic amides are known to promote the hydroxylation of the C(sp2)-H bond enabling five-membered ring ruthenacycle intermediates, the cyclic imides studied herein enabled the hydroxylation of the C(sp2)-H bond via larger six-membered ruthenacycle intermediates. Furthermore, monohydroxylated products were exclusively obtained (even in the presence of overstoichiometric amounts of reagents), which was rationalized by the difficulty to accommodate coplanar intermediates once the first hydroxyl group was introduced into the substrate. The same reactivity was observed in the presence of palladium catalysts.

Unmasking Amides: Ruthenium-Catalyzed Protodecarbonylation of N-Substituted Phthalimide Derivatives

The unprecedented transformation of a wide range of synthetically appealing phthalimides into amides in a single-step operation has been achieved in high yields and short reaction times using a ruthenium catalyst. Mechanistic studies revealed a unique, homogeneous pathway involving five-membered ring opening and CO2 release with water being the source of protons.

Ruthenium(II)-catalyzed N-substituted phthalimide synthesis via C-H activation/[3+2] annulation

Ruthenium-catalyzed intermolecular [3 + 2] annulation pathway for aromatic acids with isocyanates to afford N-substituted phthalimide in one step is demonstrated, which provides an efficient process to direct preparation of phthalimide from commercially a

A rhodium-catalyzed cascade cyclization: Direct synthesis of N-substituted phthalimides from isocyanates and benzoic acids

A rhodium(III)-catalyzed amidation between benzoic acids and isocyanates via direct functionalization of an ortho C-H bond followed by intramolecular cyclization is described. This cascade cyclization affords N-substituted phthalimides in one step in 26-91% yields. The reaction is highly atom-economical, since no theoretical waste except for water is generated in the reaction.

Preparation of N-Substituted Phthalimides by Palladium-Catalyzed Carbonylation and Coupling of o-Dihalo Aromatics and Primary Amines

A novel method for the formation of N-substituted phthalimides is described which is based on the palladium-catalyzed carbonylation and coupling of o-dihalo aromatics and primary amines.Optimal conditions established for the reaction using o-diiodobenzene and aniline were DMAc (0.2 M), 115 deg C, 90 psi of CO, 3 percent PdCl2L2, and 2.4 equiv of DBU.This process is tolerant of a wide variety of functional groups and gives good yields of the desired products.Variables such as temperature, catalyst type and loading, CO pressure, solvent, and base were examined to optimize this reaction.The reaction of aniline with 1,2-dibromocyclopentene under similar conditions gave a variety of products.