33608-93-4

Upstream product

• 103-82-2 phenylacetic acid 
• 136918-14-4 phthalimide 
• 1225463-02-4 2-iodo-N-methoxybenzamide 
• 536-74-3 phenylacetylene 
• 65-85-0 benzoic acid 
• 14178-42-8 2-benzamidopyridine 1-oxide 
• 33578-05-1 methyl 2-(phenylethynyl)benzoate 
• 1084-95-3 2-(2'-phenylethynyl)benzoic acid 
• 60901-21-5 o-styrylbenzoic acid 
• 100-52-7 benzaldehyde 
• 20871-31-2 2,3-dihydro-3-hydroxy-3-(phenylmethyl)-1H-isoindol-1-one 
• 5159-41-1 2-iodobenzyl alcohol 
• 891194-31-3 C₁₁H₁₂INO₄ 
• 891194-28-8 methyl 1-oxo-1,3-dihydro-2H-isoindole-2-carboxylate 

Downstream Products

• 40523-32-8 3-(phenylmethylene)isoindol-1-one 

Relevant academic research and scientific papers

Stepwise synthesis and spectral characteristics of meso-trans-diphenyldi(1- naphthyl)tetrabenzoporphin and its zinc complex

A reaction of phthalimide with phenylacetic acid in the presence of zinc oxide furnished 3-oxoisoindolenyl-3′-oxoisoindolinylidene-1,1′- benzylidine which at heating with 1-naphthylacetic acid in the presence of zinc oxide provided zinc meso-trans-diphenyldi(1-naphthyl)tetrabenzoporphin complex. Proceeding from this compound a meso-trans-diphenyldi(1-naphthyl) tetrabenzoporphin was prepared. The spectral characteristics of compounds obtained were studied.

Copper-mediated oxidative C-H/N-H activations with alkynes by removable hydrazides

The efficient copper-mediated oxidative C-H alkynylation of benzhydrazides was accomplished with terminal alkynes. Thus, a heteroaromatic removable N-2-pyridylhydrazide allowed for domino C-H/N-H functionalization. The approach featured remarkable functional group compatibility and ample substrate scope. Thereby, highly functionalized aromatic and heteroaromatic isoindolin-1-ones were accessed with high efficacy with rate-limiting C-H cleavage.

Synthesis of Secondary Unsaturated Lactams via an Aza-Heck Reaction

The preparation of unsaturated secondary lactams via the palladium-catalyzed cyclization of O-phenyl hydroxamates onto a pendent alkene is reported. This method provides rapid access to a broad range of lactams that are widely useful building blocks in alkaloid synthesis. Mechanistic studies support an aza-Heck-type pathway.

Cobalt(II)-Catalyzed Csp2-H Alkynylation/Annulation with Terminal Alkynes: Selective Access to 3-Methyleneisoindolin-1-one

A highly efficient cobalt(II)-catalyzed alkynylation/annulation of terminal alkynes assisted by an N,O-bidentate directing group is described. This protocol is characterized by wide substrate scope utilizing cheap cobalt catalysts, and offers a new approa

Reductive coupling of phthalimides with ketones and aldehydes by low-valent titanium: One-pot synthesis of alkylideneisoindolin-1-ones

The reductive coupling of phthalimides with ketones and aldehydes by Zn-TiCl4 in THF gave two- and four-electron reduced products, 3-hydroxy-3-(1-hydroxyalkyl)isoindolin-1-ones and alkylideneisoindolin-1-ones, selectively by controlling the rea

Photo-induced sonogashira C-C coupling reaction catalyzed by simple copper(I) chloride salt at room temperature

The conventional thermal Sonogashira C-C coupling reaction requires the use of a palladium catalyst and a large amount of ligands. Although there were a few reports describing the use of inexpensive metal catalysts, such as, copper (Cu), iron (Fe), and nickel (Ni), for replacement of palladium (Pd) in the Sonogashira reactions, it was later questioned that the observed effects were due to ppb levels contamination of Pd present in the reagents used in the reactions. Herein, we report that simple copper(I) chloride (CuCl) salt, in the absence of Pd and ligands, can catalyze the Sonogashira reaction with high yields (80-99%) under blue LED light irradiation at room temperature. Control experiments show that no cross-coupling product was formed, when palladium(II) chloride (PdCl2) was used to replace CuCl as a catalyst. A series of electron-rich and electron-poor substituted aryl halides (bromides and iodides) as well as aryl- and alkylacetylenes are examined and the reaction mechanism is discussed.

Photodecarboxylative benzylations of phthalimide in pH 7 buffer: A simple access to 3-arylmethyleneisoindolin-1-ones

Photoadditions of phenylacetates to phthalimide in pH 7 buffer solution give the corresponding benzylated-hydroxyphthalimidines in moderate to high yields of up to 94%. In a micro-structured reactor, higher conversions and purities are achieved. With branched phenylacetates, photoaddition affords diastereoisomeric mixtures with low to moderate de values. Subsequent acid-catalyzed dehydration furnishes the corresponding 3- arylmethyleneisoindolin-1-ones in good to excellent yields and with high E-selectivities. Irradiation of the parent 3-phenylmethyleneisoindolin-1-one under oxidative conditions only leads to cis/trans-isomerization.

A stereoselective synthesis of (Z)-3-aryl and alkylmethylidene-1H- isoindolin-1-ones

A series of Z-configured (hetero)aryl and alkylmethylideneisoindolin-1-ones has been efficiently prepared by treatment of N-methoxycarbonylisoindolin-1- ones with a base and reaction with selected aldehydes. The parent N-acylated isoindolin-1-ones have be

SET photochemistry of phthalimide anion and its reactivity with hydrogen donors

The investigation of the photochemistry of phthalimide anion has uncovered its exceptional reactivity with hydrogen donors such as alcohols, toluene, ethers and amines. Photoreactions can be conducted to high conversions and photoadducts are formed in high yield and with predictable regioselectivity. Exploratory studies have revealed that SET from the excited phthalimide anion to phthalimide is a thermodinamically favourable step that produces the electrophilic phthalimidyl radical and is the key step of the process.

A Novel Diphenyl Phosphorazidate Catalysed Reaction of 3-Aryl-3,4-dihydro-1-oxo-1H-2-benzopyran-4-carboxylic Acids

Reaction of 3-(3',4'-dimethoxyphenyl)-(I) and 3-phenyl-(II)-3,4-dihydro-1-oxo-1H-2-benzopyran-4-carboxylic acids with diphenyl phosphorazidate takes an unusual course to form 2,3-dihydro-3-arylmethylene-1H-isoindole-1-ones (III and IV), the formation of w