40523-35-1

Upstream product

• 4770-23-4 3-benzyl-3-hydroxy-2-methyl-1,3-dihydroisoindol-1(3H)-one 
• 122889-70-7 2-Bromo-N-methyl-N-phenylacetyl-benzamide 
• 5342-91-6 2-methylisoindolin-1-one 
• 100-52-7 benzaldehyde 
• 110166-72-8 2-(2'-phenylethynyl)-N-methyl benzamide 
• 550-44-7 N-methylphthalimide 
• 206365-69-7 3-(hydroxy(phenyl)methyl)-2-methylisoindolin-1-one 
• 4702-13-0 N-phthaloylglycine 
• 13005-36-2 potassium phenylacetate 
• 144175-21-3 N-(diphenyloxophosphinyl)methyl-N-methyl-2-bromobenzamide 
• 95840-09-8 C₂₃H₁₉NOS 

Downstream Products

• 40523-36-2 (Z)-3-benzylidene-2-methyl-2,3-dihydro-1H-isoindolin-1-one 

Relevant academic research and scientific papers

Diastereoselective addition of metalated isoindolin-1-ones to aldehydes. Stereoselective preparation of (E)-3-arylideneisoindolin-1-ones

Lithiated isoindolinones react with aromatic aldehydes to afford 3-hydroxybenzyl derivatives with high diastereoselectivity. Dehydration of erythro and threo adducts through an E1cb mechanism gives rise indiscriminately to the (E)-arylideneisoindolinones.

Selective cyclization of alkynols and alkynylamines catalyzed by potassium tert-butoxide

Potassium tert-butoxide (t-BuOK) was found to be an effective catalyst for the cyclization of aromatic alkynols and alkynylamines. In the presence of 10 mol % t-BuOK, a range of alkynols were converted to the corresponding exo-cyclic enol ethers as pure Z

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

Electroreductive intermolecular coupling of phthalimides with aldehydes: Application to the synthesis of alkylideneisoindolin-1-ones

The electroreduction of N-methyl, N-p-anisyl, and N-unsubstituted phthalimides with aldehydes in the presence of chlorotrimethylsilane and triethylamine gave intermolecularly coupled products, 3-hydroxy-3-(1- hydroxyalkyl)isoindolin-1-ones. The coupling p

Microphotochemistry: 4,4′-dimethoxybenzophenone mediated photodecarboxylation reactions involving phthalimides

A series of 4,4'-dimethoxybenzophenone mediated intra- and intermolecular photodecarboxylation reactions involving phthalimides have been examined under microflow conditions. Conversion rates, isolated yields and chemoselectivities were compared to analogous reactions in a batch photoreactor. In all cases investigated, the microreactions gave superior results thus proving the superiority of microphotochemistry over conventional technologies.

An efficient one-pot synthesis of 3-(aryl and alkyl)methylene-1H-isoindolin-1-ones via aryne cyclization and horner reaction of o-(and m-) halogeno-N-phosphorylmethylbenzamide derivatives

A series of 3-(alkyl and aryl)methylene-2,3-dihydro-1H-isoindol-1-one derivatives was synthesized by a one-pot reaction sequence involving lithiation of 2- (or 3-)halogeno-N-phosphoryl-methylbenzamides, cyclization of the aryne intermidiate, metal migration and Horner reaction of the resulting phosphorylated aminocarbanion with selected aromatic and aliphatic aldehydes.

Photochemical Reaction of Phthalimides and Dicyanophthalimides with Benzylic Donors

Irradiation of phthalimides in the presence of benzylic donors PhCRHX (R = H, Ph, X = H, SiMe3, CHPh2, proceeds via electron transfer and radical cation cleavage, resulting in benzylation at the carboximide moiety to yield 3-benzyl-3-hydroxyisoindol-3-ones.With 4,5-dicyanophthalimides substitution of benzyl for a cyano group is a competitive, and in some cases predominating, pathway.A rationalization is proposed on the basis of the in cage vs out of cage radical cation cleavage.In the first mechanism, the radical anion of the dicyanophthalimide, where spin and charge are differently located, probably assists the radical cation fragmentation.

AROMATIC HETEROANNULATION VIA ORTHO LITHIATION-CYCLIZATION OF N-ACYL-2-BROMOBENZAMIDES

N-acyl-2-bromobenzamides participate in metal-halogen exchange with n-BuLi to form N-acyl-2-lithiobenzamides, which undergo cyclization to afford 3-alkylidenephtalimides.

PHOTOREACTIONS OF PHTHALIMIDE-THIETANES: FISSION OF THE THIETANE RING AND FORMATION OF 1,2-DITHIANES

Photolysis of N-methylmonothiophthalimide (1) in the presence of thietane (4) gave 1,2-dithiane (5) and 1,3-dithiane (6).The formation of 1,2-dithianes in the photoreaction of 1 with styrene derivatives (2) is explained in terms of the intermediacy of the phthalimide-thietanes.Photolysis of the thietane ring is also described.