21815-18-9

Usage

Chemical Properties

grey to slightly purple powder

Synthesis Reference(s)

Synthesis, p. 753, 1981 DOI: 10.1055/s-1981-29592

InChI:InChI=1/C18H11NO2/c20-17-15-10-12-6-4-5-7-13(12)11-16(15)18(21)19(17)14-8-2-1-3-9-14/h1-11H

Upstream product

• 941-69-5 N-phenyl-maleimide 
• 13209-15-9 1,2-bis(dibromomethyl)benzene 
• 5959-52-4 2-Amino-3-naphthoic acid 
• 103-71-9 phenyl isocyanate 
• 93-09-4 naphthalene-2-carboxylate 
• 716-39-2 2,3-Naphthalenedicarboxylic anhydride 
• 68-12-2 N,N-dimethyl-formamide 
• 201230-82-2 carbon monoxide 
• 27715-43-1 2,3-diiodonaphthalene 
• 62-53-3 aniline 
• 2169-87-1 naphthalene-2,3-dicarboxylic acid 
• 7362-04-1 2-phenyl-2,3-dihydro-benzo[f]isoindol-1-one 

Relevant academic research and scientific papers

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.

MEDICINAL COMPOSITION

It is to provide a cyclic imide derivative which is useful as an active ingredient of a pharmaceutical composition. A pharmaceutical composition which comprises, a cyclic imide derivative represented by the general formula (I): wherein Q 1is a single bond,--CH 2--,--O--,--S--or--NH--, each of Q 2and Q 3is--C(O)--,--C(S)--or--CH 2--, provided that at least one of Q 2and Q 3is--C(O)--or--C(S)--, Z is a single bond or a lower alkanediyl group, R is an aryl group which may be substituted or a cycloalkyl group which may be substituted, X is a nitro group, an amino group which may be acylated, a cyano group, a trifluoromethyl group, a hydroxyl group, a halogen atom, an alkyl group, an alkoxy group or an alkylthio group, m is an integer of from 0 to 4, and when m is 2 or above, X may be the same or different, or its salt.

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.