2141-99-3

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
2-tert-butyl-1H-isoindole-1,3(2H)-dione is utilized as a key intermediate in the synthesis of various pharmaceuticals and agrochemicals due to its ability to form new chemical entities that can possess a range of biological activities.
Used in Anticancer Research:
In the field of oncology, tBuI is employed as a precursor in the development of molecules with potential anticancer properties, targeting the synthesis of compounds that can combat cancer cells.
Used in Antiviral and Antibacterial Research:
2-tert-butyl-1H-isoindole-1,3(2H)-dione also serves as a building block in the creation of molecules with antiviral and antibacterial capabilities, contributing to the development of new treatments for infectious diseases.
Used in Antioxidant Compound Development:
As a powerful radical scavenger, 2-tert-butyl-1H-isoindole-1,3(2H)-dione is used in the research and development of antioxidant compounds, which are crucial for various health and industrial applications, including the prevention of oxidative damage in biological systems and the stabilization of sensitive materials.

Upstream product

• 92635-22-8 N-<(3-chloro)-propanoxy>phtalimide 
• 75-64-9 tert-butylamine 
• 85-44-9 phthalic anhydride 
• 88-67-5 2-Iodobenzoic acid 
• 64-18-6 formic acid 
• 609-67-6 2-Iodobenzoyl chloride 
• 615-42-9 1,2-Diiodobenzene 
• 201230-82-2 carbon monoxide 

Downstream Products

• 75-64-9 tert-butylamine 
• 169228-67-5 2-acetyl-N-tert-butylbenzoylamide 

Relevant academic research and scientific papers

A hitherto undescribed addition of the lithium salt of dimethyl methylphosphonate to N-substituted phthalimides

The hitherto unknown addition of the lithium salt of dimethyl methylphosphonate 6 to the N-substituted phthalimides 7 is described. This reaction allows the synthesis of new systems in which the phosphono group is connected to the heterocyclic skeleton of an isoindolinone at the 3-position by one methylene group.

PPh3/I2/HCOOH: An efficient CO source for the synthesis of phthalimides

A straightforward and general method has been developed for the synthesis of phthalimide derivatives from 2-iodobenzamides and PPh3/I2/HCOOH in the presence of a catalytic amount of Pd(OAc)2. The reaction results demonstrate that PPh3/I2/HCOOH is a facile, efficient and safe CO source. The whole process is carried out in toluene at 80 °C and furnishes the desired products in good to excellent yields.

Practical synthesis of phthalimides and benzamides by a multicomponent reaction involving arynes, isocyanides, and CO2/H2O

Transition-metal-free multicomponent reactions involving arynes and isocyanides with either CO2 or H2O have been reported. With CO2 as the third component, the reactions resulted in the formation of N-substituted phthalimides. The utility of water as the third component furnished benzamide derivatives in moderate to good yields. These reactions took place under mild conditions with broad scope.

Synthesis of tetrahydrophthalazine and phthalamide (phthalimide) derivatives via palladium-catalysed carbonylation of iodoarenes

1,2,3,4-Tetrahydrophthalazin-1-one and 1,2,3,4-tetrahydrophthalazin-1,4- dione derivatives were synthesised in high (up to 85%) and low yields using 2-iodobenzyl bromide and 1,2-diiodobenzene as bifunctional substrates, respectively. Iodoarenes, carbon monoxide and various hydrazine derivatives as N-nucleophiles were used in a three-component palladium-catalysed cascade hydrazinocarbonylation. A similar palladium-catalysed reaction, the aminocarbonylation of 1,2-diiodobenzene, resulted mainly in the formation of two types of major products depending on the amine N-nucleophiles: the use of primary amines yielded N-substituted phthalimides in double carbonylation, while secondary amines react with one of the iodoarene functionalities affording the corresponding 2-iodobenzamides. Due to double carbon monoxide insertion at one or both iodoarene functionalities, ketocarboxamide-carboxamide or bis-ketocarboxamide derivatives could be isolated by the modification of the reaction conditions. Some mechanistic details of the ring-closure reactions and the conditions leading to side-products are also discussed.

Facile syntheses and characterization of hyperbranched poly(ester-amide)s from commercially available aliphatic carboxylic anhydride and multihydroxyl primary amine

A new method for synthesis of novel hyperbranched poly(ester-amide)s from commercially available AA′ and CBx type monomers has been developed on the basis of a series of model reactions. The hyperbranched poly(ester-amide)s with multihydroxyl end groups are prepared by thermal polycondensation of carboxyl anhydrides (AA′) and multihydroxyl primary amine (CBx) without any catalyst and solvent. The reaction mechanism in the initial stage of polymerization was investigated with in situ 1H NMR. In the initial stage of the reaction, primary amino groups of 2-amino-2-ethyl-1,3-propanediol (AEPO) or tris(hydroxymethyl)aminomethane (THAM) react rapidly with anhydride, forming an intermediate which can be considered as a new ABx type monomer. Further self-polycondensation reactions of the ABx molecules produce hyperbranched polymers. Analysis using 1H and 13C NMR spectroscopy revealed the degree of branching of the resulting polymers ranging from 0.36 to 0.55. These hyperbranched poly(ester-amide)s contain configurational isomers observed by 13C and DEPT 13C NMR spectroscopy, possess high molecular weights with broad distributions and display glass-transition temperatures (Tgs) between 7 and 96°C. The thermogravimetric analytic measurements revealed the decomposition temperature at 10% weight-loss temperatures (Td10%) ranging from 212 to 325°C. Among the hyperbranched poly(ester-amide)s obtained, the polymers with cyclohexyl molecular skeleton structure exhibit the lowest branching degree, the highest glass-transition temperatures, and the best thermal stability.

Investigation of the thionation reaction of cyclic imides

A series of monothioimides and dithioimides were synthesised using Lawesson's reagent. It has been found that two main effects affect thionation reaction. The high polarity of carbonyl groups leads to good yields of mono- and dithioimides. On the other hand, steric hindrance in the vicinity of the carbonyl group strongly inhibits the replacement of the oxygen atom by sulfur.

N-Alkylphthalimides: Structural requirement of thalidomidal action on 12-O-tetradecanoylphorbol-13-acetate-induced tumor necrosis factor α production by human leukemia HL-60 cells

Phthalimide analogs N-substituted with n-butyl, tert-butyl, hexyl and adamantyl groups were designed and prepared as simplified analogs of thalidomide and methylthalidomide. All the compounds prepared except N-n-butylphthalimide showed thalidomidal activity on 12-O-tetradecanoylphorbol-13-acetate-induced tumor necrosis factor (TNF)-α production by human leukemia HL-60 cells. Among the investigated compounds, including thalidomide and methylthalidomide, N-adamantylphthalimide showed the most potent TNF-α production-enhancing activity.

Studies on the Chemistry of Isoindoles and Isoindolenines, XXXV. 1-Alkoxy-2-alkyl-2H-isoindoles - o-Quinonoid Hetarenes with Unsymmetric Structure

3-Alkoxy-2-methyl-1H-isoindolium salts have been prepared either via regioselective O-alkylation of the corresponding 2-alkyl-isoindoline-1-ones or via regioselective N-alkylation of 3-alkoxy-1H-isoindoles with trialkyloxonium tetrafluoroborates or with alkyl trifluoromethanesulfonates.Deprotonation of these stable precursors leads to the generation of reactive 1-alkoxy-2-alkyl-2H-isoindoles in solution.Reactions with CC-dienophiles (N-substituted maleic imides) give rise to the formation of 1:2-adducts.The two step reaction comprises Michael-addition and Diels-Alder-addition; the isolation of an initially formed 1:1-adduct is possible in the case of steric hindrance.Constitution and configuration of a representative 1:2-adduct has been established by X-ray crystal structure determination. - Keywords: 1-Alkoxy-2-alkyl-2H-isoindoles, Generation and Characterization, Addition and Cycloaddition Reactions with CC-Dienophiles

THE REACTION OF AMINES WITH PHTALIMIDE DERIVATIVES. A CONVENIENT SYNTHESIS OF ISOXAZOLIDINE

The reaction of tert-butylamine, isoxazolidine and hydrazine with N-phtalimide is investigated.A convenient synthesis of oxazolidine is described.