- Syntheses, structural studies and spectroscopic characterisation of pyridyl-phthalimide complexes of fac-(CO)3ReI-diimines
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The mono-dentate ligands, 3-aminomethyl-N-phthalimido-pyridine (L1) and 3-amino-N-phthalimido-pyridine (L2), were synthesised using a solvent-free melt method. These ligands were then used to access three pairs of functionalised lumi
- Thorp-Greenwood, Flora L.,Coogan, Michael P.,Hallett, Andrew J.,Laye, Rebecca H.,Pope, Simon J.A.
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Read Online
- On the Photochemical Reactivity of Phthalonimide
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The occurence of an electrophilic phthalonimidyl radical is proposed to account for the N-arylation products obtained by irradiation of phthalonimide in benzene in the presence of an amine and oxygen.Normal carbonyl reactivity is observed in the photochemical reactions of phthalonimide with furan (oxetane formation) and hydrogen donors (photoreduction).
- Suau, Rafael,Villatoro, Ezequiel P. de Inestrosa
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Read Online
- Nitrogen-centered radical-mediated C-H imidation of arenes and heteroarenes via visible light induced photocatalysis
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The C-H imidation of arenes and heteroarenes has been achieved via visible light induced photocatalysis. In the presence of an iridium(iii) photoredox catalyst, the reaction of aromatic substrates with N-chlorophthalimide furnishes the N-aryl products at room temperature through a nitrogen-centered radical mediated aromatic substitution.
- Kim, Hyejin,Kim, Taehoon,Lee, Dong Gil,Roh, Sang Weon,Lee, Chulbom
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supporting information
p. 9273 - 9276
(2014/08/05)
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- N-acyloxyphthalimides as nitrogen radical precursors in the visible light photocatalyzed room temperature C-H amination of arenes and heteroarenes
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This paper reports a room temperature visible light photocatalyzed method for the C-H amination of arenes and heteroarenes. A key enabling advance in this work is the design of N-acyloxyphthalimides as precursors to nitrogen-based radical intermediates for these transformations. A broad substrate scope is presented, including the selective meta-amination of pyridine derivatives. A radical aromatic substitution mechanism is proposed.
- Allen, Laura J.,Cabrera, Pablo J.,Lee, Melissa,Sanford, Melanie S.
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supporting information
p. 5607 - 5610
(2014/05/06)
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- Immobilized palladium metal containing ionic liquid catalyzed one step synthesis of isoindole-1,3-diones by carbonylative cyclization reaction
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Immobilized palladium metal containing ionic liquid (ImmPd-IL) catalyzed carbonylative cyclization reaction of 2-iodobenzoic acid and primary amine provided N-substituted isoindole-1,3-dione derivatives in good to excellent yield. The influence of various reaction parameters including the effect of base, solvent, temperature, time and CO pressure on carbonylative cyclization reaction using ImmPd-IL catalyst was investigated. Using optimized reaction parameters different aromatic, aliphatic and heterocyclic N-substituted isoindole-1,3-dione derivatives were synthesized from corresponding aryl amines. The developed protocol is heterogeneous, phosphine free and requires attainable reaction conditions like atmospheric CO pressure and lesser reaction time. The scope of the developed protocol was also extended for the synthesis of N-substituted isoindole-1,3-diones from methyl-2-iodobenoate and 1,2-diiodo benzene. The ImmPd-IL catalyst was recyclable up to four consecutive cycles and recycled catalyst was characterized by XPS analysis.
- Khedkar, Mayur V.,Shinde, Ajinkya R.,Sasaki, Takehiko,Bhanage, Bhalchandra M.
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- Palladium on carbon: An efficient, heterogeneous and reusable catalytic system for carbonylative synthesis of N-substituted phthalimides
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The application of palladium on carbon (Pd/C) as a heterogeneous recyclable catalyst was investigated for the double carbonylation of o-dihaloarenes with amines providing excellent yield of N-substituted phthalimides in shorter reaction time as compared to earlier reported homogeneous protocols. Furthermore, the scope of the developed protocol was applied for the synthesis N-substituted phthalimides from o-halobenzoates and o-halobenzoic acid via a single step carbonylative cyclization reaction. The developed methodology describes an efficient one-step approach for the synthesis of an important class of heterocycles and tolerates a wide variety of functional groups. It circumvents the use of phosphine ligands with an additional advantage of catalyst recyclability for up to eight consecutive cycles. Copyright
- Khedkar, Mayur V.,Khan, Shoeb R.,Sawant, Dinesh N.,Bagal, Dattatraya B.,Bhanage, Bhalchandra M.
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supporting information; experimental part
p. 3415 - 3422
(2012/02/05)
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- New anti-inflammatory N-pyridinyl(alkyl)phthalimides acting as tumour necrosis factor-α production inhibitors
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This paper describes the synthesis of N-pyridinyl(alkyl)phthalimides related to N-phenyl-4,5,6,7-tetrafluorophthalimides known to be inhibitors of tumour necrosis factor-α (TNFα) production. Pharmacomodulation at the phthalimidic nitrogen led to the selection of two pharmacophoric fragments (2,4-lutidinyl and β-picolyl), allowing significant inhibition of TNFα production (compounds 12 and 17). Variation of the substituents linked to the homocycle of their phthalimide scaffold indicated that high (TNFα production) inhibitory potency could be achieved, notably by 5-fluoro, 4- or 5-nitro, 5-amino and especially tetrafluoro substitution. The most active compound, N-(pyridin-3-ylmethyl)-4,5,6,7-tetrafluorophthalimide (32) (84% inhibition at 10 μM), also produced an anti-oedematous effect in the PMA-induced mouse-ear swelling test. Although less active than dexamethasone, it exerted a marked reduction in ear thickness after oral administration (63% vs. 85% for dexamethasone at 0.2 mM kg-1) and remained efficient after topical application (46% vs. 96% for the dexamethasone). It also induced potent inhibition in the rat carrageenan foot oedema test with an ID50 (0.14 μM kg-1) comparable with that of N-(2,6-diisopropylphenyl)phthalimide (4) (0.15 μM kg-1).
- Collin, Xavier,Robert, Jean-Michel,Wielgosz, Gaetane,Le Baut, Guillaume,Bobin-Dubigeon, Christine,Grimaud, Nicole,Petit, Jean-Yves
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p. 639 - 649
(2007/10/03)
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