2133-65-5Relevant articles and documents
Carbon monoxide-free one-step synthesis of isoindole-1,3-diones by cycloaminocarbonylation of o-haloarenes using formamides
Sawant, Dinesh N.,Wagh, Yogesh S.,Bhatte, Kushal D.,Bhanage, Bhalchandra M.
, p. 6719 - 6724 (2011)
A new carbon monoxide-free, solvent-free, single step protocol for the synthesis of isoindole-1,3-diones from o-haloarenes using palladium acetate and xantphos catalysis is reported. The wider applicability of this protocol for several types of o-iodoarenes and a few o-bromoarenes makes it attractive. Aryl iodides and aryl bromides provided moderate to excellent yields of up to 93 %.
[3 + 2] Cycloaddition with photogenerated azomethine ylides in β-cyclodextrin
Basari?, Nikola,Mandi?, Leo,Sohora, Margareta
, p. 1296 - 1304 (2020)
Stability constants for the inclusion complexes of cyclohexylphthalimide 2 and adamantylphthalimide 3 with β-cyclodextrin (β-CD) were determined by 1H NMR titration, K = 190 ± 50 M?1, and K = 2600 ± 600 M?1, respectively. Photochemical reactivity of the inclusion complexes 2&at;β-CD and 3&at;β-CD was investigated, and we found out that β-CD does not affect the decarboxylation efficiency, while it affects the subsequent photochemical H-abstraction, resulting in different product distribution upon irradiation in the presence of β-CD. The formation of ternary complexes with acrylonitrile (AN) and 2&at;β-CD or 3&at;β-CD was also essayed by 1H NMR. Although the formation of such complexes was suggested, stability constants could not be determined. Irradiation of 2&at;β-CD in the presence of AN in aqueous solution where cycloadduct 7 was formed highly suggests that decarboxylation and [3 + 2] cycloaddition take place in the ternary complex, whereas such a reactivity from bulky adamantane 3 is less likely. This proof of principle that decarboxylation and cycloaddition can be performed in the β-CD cavity has a significant importance for the design of new supramolecular systems for the control of photoreactivity.
Wavelength dependent photoextrusion and tandem photo-extrusion reactions of ninhydrin bis-acetals for the synthesis of 8-ring lactones, benzocyclobutenes and orthoanhydrides
George, Michael W.,Hanson-Heine, Magnus W. D.,Harrowven, David C.,Kayal, Surajit,Light, Mark E.,Raimbach, William A. T.,Sun, Wei,Sun, Xue-Zhong
, p. 1546 - 1549 (2022/02/14)
Ninhydrin bis-acetals give access to 8-ring lactones, benzocyclo-butenes and spirocyclic orthoanhydrides through photoextrusion and tandem photoextrusion reactions. Syntheses of fimbricalyxlactone B, isoshihunine and numerous biologically-relevant heteroc
Metal-free Photocatalytic Intermolecular anti-Markovnikov Hydroamination of Unactivated Alkenes
Li, Juncheng,Wang, Ting,Zhao, Gaoyuan
supporting information, p. 2650 - 2654 (2021/06/25)
The development of photocatalytic intermolecular hydroamination reaction between N-aminated dihydropyridines and unactivated alkenes is reported. Metal-free co-catalysts, rhodamine 6G and thiophenol, in presence of visible light are used to initiate the process. The transformation shows a broad substrate scope, both alkenes and amidyl radical can act as coupling partners. The radical strategy provides excellent anti-Markovnikov selectivity and regioselectivity in diene substrates.
Photophysical properties and electron transfer photochemical reactivity of substituted phthalimides
Mandi?, Leo,D?eba, Iva,Jadre?ko, Dijana,Mihaljevi?, Branka,Biczók, László,Basari?, Nikola
, p. 17252 - 17266 (2020/11/02)
The photochemical reactivity and photophysical and electrochemical properties of a series of N-adamantylphthalimides bearing carboxylic functional groups were investigated. Upon irradiation (with or without a triplet sensitizer), the compounds undergo decarboxylation via photoinduced electron transfer (PET) from the carboxylate to the phthalimide. UV-vis and fluorescence pH titrations were used to determine pKa values for the prototropic forms, which were put in connection with the quantum yields of the reaction (ΦR). The compounds bearing electron donors OH and OCH3 at the phthalimide 4 position are fluorescent (ΦF = 0.02-0.49) and PET takes place from both singlet and triplet excited states. The estimated rate constants for PET in the singlet excited states for the methoxy- A nd amino-substituted phthalimides are (2.0 ± 0.1) × 109 s-1 and (3.4 ± 1.0) × 107 s-1, respectively. Laser flash photolysis (LFP) was conducted to characterize the triplet excited states, which are populated less efficiently for compounds with electron donors. The PET is reversible and the overall ΦR depends on the rates for back electron transfer, protonation of the phthalimide radical anion and decarboxylation. The plausible photochemical and photophysical pathways depend on the phthalimide substituents, which is important for the use of phthalimide derivatives in organic synthesis and photocatalysis. This journal is
Graphene Oxide: A Metal-Free Carbocatalyst for the Synthesis of Diverse Amides under Solvent-Free Conditions
Patel, Khushbu P.,Gayakwad, Eknath M.,Patil, Vilas V.,Shankarling, Ganapati S.
supporting information, p. 2107 - 2116 (2019/03/26)
An environmentally friendly, inexpensive, carbocatalyst, graphene oxide (GO) promoted efficient, metal-free transamidation of various carboxamides with aliphatic, cyclic, and aromatic amines is demonstrated. The protocol is equally applicable to phthalimide, urea, and thioamide determining its adaptability. The oxygenated functionalities such as carbonyl (?C=O), epoxy (?O?), carboxyl (?COOH) and hydroxyl (?OH), present on graphene oxide surface impart acidic properties to the catalyst. The graphene oxide being heterogeneous in nature, work efficiently under solvent-free reaction conditions providing desired products in good to excellent yields. The one-pot synthesis of 2,3-Dihydro-5H-benzo[b]-1,4-thiazepin-4-one moiety by GO catalyzed Aza Michael addition followed by intramolecular transamidation is also described. A plausible reaction mechanistic pathway involving H-bonding is discussed. The graphene oxide can be recycled and reused up to five cycles without much loss in catalytic activity. (Figure presented.).
PPh3/I2/HCOOH: An efficient CO source for the synthesis of phthalimides
Wang, Yingying,Zhou, Yang,Lei, Min,Hou, Jinjun,Jin, Qinghao,Guo, Dean,Wu, Wanying
, p. 1180 - 1185 (2019/01/26)
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.
Method for constructing N-cyclohexyl phthalimide in one step from imine as a starting material
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Paragraph 0022; 0023; 0035-0038; 0041-0046; 0049-0053, (2019/01/16)
The invention discloses a method for constructing N-cyclohexyl phthalimide in one step from imine as a starting material. According to the method, (E)-N-cyclohexyl-1-phenylmethylimine is used as a reaction raw material and subjected to carbonylation react
The aminocarbonylation of 1,2-diiodoarenes with primary and secondary amines catalyzed by palladium complexes with imidazole ligands
Wójcik, Przemys?aw,Trzeciak, Anna M.
, p. 73 - 83 (2018/05/22)
The efficient carbonylative cyclization of 1,2-diiodobenzene with different primary and secondary amines was performed using a palladium complex with an imidazole ligand, PdCl2(BIM)2, as a catalyst. In reactions performed at 1 atm of CO with primary amines, phthalimides were obtained as the only products with yields of up to 100% in 4 h. An even shorter time, 1 h, was sufficient to obtain the same products employing methyl-2-iodobenzoate as a substrate instead of 1,2-diiodobenzene. In an analogous reaction with secondary amines, 1,2-diiodobenzene was converted to three products, formed in amounts dependent on the reaction conditions. The presence of Pd NPs and soluble palladium intermediates indicated their participation in the catalytic reaction.
Intermolecular Radical Mediated Anti-Markovnikov Alkene Hydroamination Using N-Hydroxyphthalimide
Lardy, Samuel W.,Schmidt, Valerie A.
supporting information, p. 12318 - 12322 (2018/10/02)
An intermolecular anti-Markovnikov hydroamination of alkenes has been developed using triethyl phosphite and N-hydroxyphthalimide. The process tolerates a wide range of alkenes, including vinyl ethers, silanes, and sulfides as well as electronically unbiased terminal and internal alkenes. The resultant N-alkylphthalimides can readily be transformed to the corresponding primary amines. Mechanistic probes indicate that the process is mediated via a phosphite promoted radical deoxygenation of N-hydroxyphthalimide to access phthalimidyl radicals.
