26486-96-4

Upstream product

• 5022-29-7 N-ethylphthalimide 
• 2051-90-3 Dichlorodiphenylmethane 
• 109-90-0 ethyl isocyanate 
• 85-52-9 2-Benzoylbenzoic acid 
• 75-04-7 ethylamine 
• 14321-27-8 N-ethylbenzylamine 
• 393-52-2 2-Fluorobenzoyl chloride 
• 22103-85-1 2-benzoylbenzoyl chloride 
• 733-85-7 2-ethyl-3-methoxy-3-phenyl-2,3-dihydro-isoindol-1-one 
• 18852-53-4 3-chloro-3-phenylphthalide 

Downstream Products

• 85-52-9 2-Benzoylbenzoic acid 
• 733-85-7 2-ethyl-3-methoxy-3-phenyl-2,3-dihydro-isoindol-1-one 

Relevant academic research and scientific papers

Base-promoted cascade C-C coupling/N-α-sp3C-H hydroxylation for the regiospecific synthesis of 3-hydroxyisoindolinones

A base-promoted cascade reaction for the regiospecific synthesis of substituted 3-hydroxyisoindolinones under transition-metal-free conditions is developed. The base-mediated C-C bond coupling and N-α-sp3C-H bond hydroxylation are involved in t

Hydrogenolysis of the C-O bond of hydroxylactams as a convenient method for the synthesis of substituted isoindolin-1-ones

A simple and efficient method for the synthesis of isoindolin-1-ones containing alkyl or aryl substituents at positions 2 and (or) 3 was suggested. The method is based on the earlier unknown Pd0-catalyzed hydrogenolysis of hydroxylactams.

Total spontaneous resolution by deracemization of isoindolinones

Preferential crystallization is a powerful tool to obtain optically active materials from racemic mixtures without any chiral source, and has been utilized widely for optical resolution on large scales for example in industrial processes.[ 1] To resolve optically active materials by crystallization efficiently, dynamic preferential crystallization involving a racemization process, a so-called total spontaneous resolution, has been developed.[2] Many efforts have been invested in new variations of this method, and the racemization processes can be classified into three groups: 1) involving an intermediate enolate anion or enol at the a-position of a carbonyl group,[3] 2) involving atropisomerism of axially chiral materials,[4] and 3) involving an equilibrium reaction via an achiral intermediate.[5-7] We have now developed a new example of total spontaneous resolution of isoindolinones that involves a combination of an intramolecular equilibrium reaction via an achiral intermediate and preferential crystallization.

Facile synthesis of non-nucleoside compounds starting from a-chlorocarbenium ions and isocyanates as potential hiv-1 reverse transcriptase inhibitors

Chloro(phenyl)carbenium hexachloroantimonate salts react with isocyanates to afford either isoindolium (1) or benzoxazinium salts (2). Addition of one equivalent of alcohol to 2 led, after hydrolysis with aq. NaOH, to the formation of benzoxazin-2-ones 3. Treatment with a large excess of alcohol transformed the salts 1 and 2 to the corresponding isoindol-1-ones 11 and the isocyanates 5, respectively. Reaction of 5 with primary amines furnished the urea derivatives 6 in good yield. The biological activity of 6a - o against HIV-1 was determined.

Photochimie organique: photolyse de O-benzoylbenzamides secondaires et tertiaires

Intramolecular photoreduction of ketones leads to a diradical likely to undergo cleavage or cyclization to yield cyclobutanols (Norrish type II reaction).Examples of intramolecular δ- or ε-H-abstraction are known to lead to 1,5- or 1,6-diradicals, the cyclization of which gives rise to five or six-membered rings.We have prepared a series of O-benzoyl-benzamides and studied their photolysis in order to establish a pathway to phenyltetrahydroisoqoinolines.We have thus prepared N-ethyl, N-isopropyl and N-benzyl-O-benzoylbenzamides and shown that in solution these compounds have a cyclic structure (3-hydroxy-3-phenylphtalimidine) in which the ketone carbonyl is hidden.These compounds are photochemically inert.Four tertiary O-benzoylbenzamides have been prepared (N,N-diethyl, N,N-di-n-butyl, N-butyl-N-methyl, and N-benzyl-N-methyl).These compounds exhibit an n?* absorption above 300 nm.Their photolysis (λ > 300 nm) gives rise in all four cases to the 3-phenylphtalide 9 and to their dimer 10 of the 3-phenylphtalid-3-yl radical (meso and d,l) mixture.Upon irradiation below 300 nm (253.7 nm in quartz), formation of the diphtalide (dimer 10), not of the phenylphtalide 9, is observed.Finally no cyclic photoproducts derived from a 1,6-diradical are observed.In thus appears that deactivation of the excited state of tertiary O-benzolylbenzamides does not occur by intramolecular abstraction of the hydrogen α to the amide nitrogen atom, but rather by homolytic cleavage of the amide C-N bond.The radical thus formed cyclizes, giving a 3-phenylphtalid-3-yl radical which further yields, either the 3-phenylphtalide 9 by hydrogen capture, or the dimer 10 by coupling.During irradiation at 253.7 nm the optical density of the solution is very high (of the order of 1000) because of the high ε values of the starting compounds.The local concentration of 3-phenylphtalid-3-yl radicals is thus high, promoting their coupling to dimer at the expense of hydrogen capture, which would lead to the 3-phenylphtalide 9.