- Synthetic analogues of the natural compound cryphonectric acid interfere with photosynthetic machinery through two different mechanisms
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A series of isobenzofuran-1(3H)-ones (phthalides), analogues of the naturally occurring phytotoxin cryphonectric acid, were designed, synthesized, and fully characterized by NMR, IR, and MS analyses. Their synthesis was achieved via condensation, aromatiz
- Teixeira, Róbson Ricardo,Pereira, Wagner Luiz,Tomaz, Deborah Campos,De Oliveira, Fabrício Marques,Giberti, Samuele,Forlani, Giuseppe
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- Association of electroanalytical and spectrophotometric methods to evaluate the antioxidant activity of isobenzofuranone in primary cultures of hippocampal neurons
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The isobenzofuran-1(3H)-ones (phthalides) exhibit various biological activities, including antioxidant activity on reactive oxygen species (ROS). An excess of ROS that cannot be naturally contained by cellular enzymatic systems is called redox imbalance,
- Coelho Nogueira, Katiane de Oliveira Pinto,Manhabosco, Taise Matte,Oliveira, Laser Ant?nio Machado,Pereira, Wagner Luiz,Ribeiro, Iara Mariana Lellis,Teixeira, Róbson Ricardo,de Brito, Ana Carolina Ferreira,dos Reis Teixeira, Aniely
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- Nuclear Magnetic Resonance (NMR), Infrared (IR) and Mass Spectrometry (MS) study of keto-enol tautomerism of isobenzofuran-1(3H)-one derivatives
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The keto-enol tautomerism of 3-(2-hydroxy-4,4-dimethyl-6-oxo-cyclohexen-1-yl)isobenzofuran-1(3H-one (1), 3-(2-hydroxy-6-oxocyclohex-1-enyl)isobenzofuran-1(3H)-one (2), 3-(2-hydroxy-4-methyl-6-oxocyclohex-1-enyl)isobenzofuran-1(3H)-one (3), 3-(2-hydroxy-5-
- Pires, Diego Arantes Teixeira,Pereira, Wagner Luiz,Teixeira, Róbson Ricardo,Figueroa-Villar, José Daniel,Nascimento, Claudia Jorge Do
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- Efficient PhB(OH)2-catalyzed one-pot synthesis of 3-substituted isoindolin-1-ones and isobenzofuran-1(3H)-ones under solvent free conditions
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An efficient and practical one-pot synthesis of 3-substituted isoindolin-1-ones and isobenzofuran-1(3H)-ones has been developed under solvent free-conditions using non-toxic and cheap phenylboronic acid as excellent catalyst. This strategy involves the sequential two-step Mannich/lactamization cascade reaction of inexpensive 2-formylbenzoic acid with primary amines and a wide variety of ketones, and an aldol/lactonization cascade reaction of 2-formylbenzoic acid with a broad range of ketones.
- Palillero-Cisneros, Angel,Bedolla-Medrano, Mercedes,Ordó?ez, Mario
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p. 4174 - 4181
(2018/06/25)
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- One-pot synthesis of isobenzofuran-1(3H)-ones using sulfuric acid immobilized on silica under solvent-free conditions and survey of third-order nonlinear optical properties
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Solvent-free synthesis of isobenzofuran-1(3H)-ones have been described via reaction of phthalaldehydic acid (2-carboxybenzaldehyde) with methylaryl or cyclic ketones using sulfuric acid immobilized on silica (H2SO4-SiO2) in excellent yields (70-88%). The catalyst can be recovered by simple filtration and reused. Also, some of these compounds has been studied the third-order nonlinear optical properties by laser Gaussian z-scan techniques.
- Maleki, Behrooz,Koushki, Ehsan,Baghayeri, Mehdi,Ashrafi, Samaneh Sedigh
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p. 2827 - 2831
(2015/06/02)
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- An efficient and green synthesis of phthalide-fused pyrazole and pyrimidine derivatives
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An efficient and green method for the synthesis of phthalide [isobenzofuran-1(3H)-one] fused pyrazoles via the catalyst-free condensation reaction of 2-formylbenzoic acid, hydrazine hydrate, and acetylenic esters in water is reported. Reaction of 2-formylbenzoic acid with 6-amino-uracils or cyclic 1,3-diketones resulted in the formation of phthalide-fused pyrimidine or cyclic 1,3-diketone derivatives.
- Motamedi, Anahita,Sattari, Elahe,Mirzaei, Peiman,Armaghan, Mahsa,Bazgir, Ayoob
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p. 2366 - 2368
(2014/05/06)
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- Synthesis and antiproliferative activity of C-3 functionalized isobenzofuran-1(3H)-ones
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A series of thirteen C-3 functionalized isobenzofuran-1(3H)-ones (phtalides) was synthesized via condensation, aromatization, and acetylation reactions. NMR (one and two dimensional experiments), IR, and mass spectrometry analysis allowed confirmation of
- Teixeira, Robson Ricardo,Bressan, Gustavo Costa,Pereira, Wagner Luiz,Joana Gasperazzo Ferreira,De Oliveira, Fabricio Marques,Thomaz, Deborah Campos
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p. 1881 - 1896
(2013/04/23)
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- Regiospecific synthesis of 3-(2,6-dihydroxyphenyl)phthalides: application to the synthesis of isopestacin and cryphonectric acid
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DBU catalyzed condensation of phthalaldehydic acids and 1,3-diketones has been developed to be a general method for the synthesis of 3-substituted phthalides. This method, in combination with mercuric acetate mediated oxidative aromatization has been util
- Mal, Dipakranjan,Pahari, Pallab,De, Saroj Ranjan
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p. 11781 - 11792
(2008/03/13)
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- Regiospecific synthesis of isopestacin, a naturally occurring isobenzofuranone antioxidant
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A DBU promoted aldol cyclocondensation of hydroxyisobenzofuranone 15 with cyclohexane-1,3-dione, followed by aromatization has resulted in the first short synthesis of isopestacin (1).
- Pahari, Pallab,Senapati, Bidyut,Mal, Dipakranjan
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p. 5109 - 5112
(2007/10/03)
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- Chemistry of dimedone--Structures of aldehyde-dimedone adducts
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Novel features in the structures and stability of products of the hoary reaction of aldehydes with dimedone are described.Dimedone and cinnamaldehyde afford the bisdimedonyl derivative 3 or the perhydrochroman 5, while 4-dimethylaminocinnamaldehyde afford
- Nagarajan, K,Shenoy, S J
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