Synthesis and Structural Study of New Saturated Isoindol-1-one Derivatives

Csende, Ferenc; Szabó, Zoltán; Stájer, Géza

doi:10.3987/com-93-6366

Cited by 17 publications

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“…Among the organic species we have synthesized, the isoindolinones are especially important. These compounds, particularly those with an alkylidene substituent in position 3 (see 6 , 11 − 13 in Schemes and ), have attracted considerable interest because of their reported pharmacological activity. − Several natural alkaloids such as neuvamine, , lennoxamine, , pictonamine, or molecules having antitumor activity contain an isoindolinone moiety. However, there are few methods reported for the synthesis of this type of compound. − …”

Section: Introductionmentioning

confidence: 99%

Depalladation Reactions of Iminoacyl- and 2-Acetylarylpalladium(II) Complexes

et al. 2003

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Reaction with Tl(TfO) (TfO = triflate, CF3SO3), in some cases in the presence of CO or EtOH, causes the depalladation of complexes trans-[Pd{C(NR)C6H4{C(O)Me}-2}Br(CNR)2] [R = 2,6-dimethylphenyl (Xy) (1a), R = t Bu (1a‘)], trans-[Pd{C(NXy)C6H(OMe)3-2,3,4-{C(O)Me}-6}Br(CNXy)2] (1b), trans-[Pd{C(NR)C6H4(CHCH2)-2}Br(CNR)2] [R = Xy (2), t Bu (2‘)], trans-[Pd{C(NXy)C(NHXy)CC6H4{C(O)NXy}-2}Br(CNXy)2] (3), trans-[Pd{C6H4{C(O)Me}-2}Br(PPh3)2] (4), and [Pd{C6H4{C(O)Me}-2}Br(bpy)] (bpy = 2,2‘-bipyridine) (5) to give organic compounds. Complexes 1a, 1a‘, and 1b react with Tl(TfO) in Me2CO or CH2Cl2 to give the isoindolinones 2-(2,6-dimethylphenyl)-3-methylene-2,3-dihydroisoindol-1-one (6a), 2-tert-butyl-3-methylene-2,3-dihydroisoindol-1-one (6a‘), and 2-(2,6-dimethylphenyl)-5,6,7-trimethoxy-3-methylene-2,3-dihydroisoindol-1-one (6b), respectively. When the reaction with 1a‘ is carried out in the presence of a small amount of EtOH, in addition to 6a‘, the isoindolinone 2-tert-butyl-3-ethoxy-3-methyl-2,3-dihydroisoindol-1-one (7) and 2-acetyl-N-tert-butylbenzamide (8) are obtained. Complex 2 reacts with Tl(TfO) in the presence of CO to give N-(2,6-dimethylphenyl)-2-vinylbenzamide (9); however, the analogous compound 2‘ reacts with Tl(TfO) to give a mixture containing ortho-cyanostyrene (10). Complex 3 reacts with Tl(TfO) to give a separable mixture of N-(2,6-dimethylphenyl)-2-(2,6-dimethylphenylamino)-2-[2-(2,6-dimethylphenyl)-3-oxo-2,3-dihydroisoindol-1-ylidene]acetamide (11) and N-(2,6-dimethylphenyl)-2-(2,6-dimethylphenylamino)-2-[2-(2,6-dimethylphenyl)-3-oxo-2,3-dihydroisoindol-1-ylidene]acetamidic acid (12). When this reaction is carried out in the presence of a small amount of EtOH, 11, 12, and its ethyl ester 13 are obtained. Complex 4 or 5 reacts with CO and Tl(TfO) in Me2CO to give 3-methylenephthalide (14) or a complex mixture, respectively. Complexes 4 and 5 react with Tl(TfO) in CH2Cl2 in the presence of a small amount of EtOH, affording 3-ethoxy-3-methyl-3H-isobenzofuran-1-one (15). The crystal and molecular structures of 6a, 6b, 8·0.11H2O, 9, 11·0.5Et2O, 13, and 14 have been determined by X-ray diffraction studies.

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Section: Introductionmentioning

confidence: 99%

Depalladation Reactions of Iminoacyl- and 2-Acetylarylpalladium(II) Complexes

et al. 2003

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“…Refluxing of a mixture of 6-azatricyclo[6.1.1.0 4,9 ]decane-6-carbaldehyde 48 and 95% formic acid for 12 hours gave a 1:1 mixture of (E)-and (Z)-9-isobutylidene-8-methyl-2-azatricyclo [29]. Elimination of a proton from 62 with triethylamine generates an anionic intermediate, which is stabilized in ethanol.…”

Section: Acid-promoted Rearrangementsmentioning

confidence: 98%

“…The reactions of cis-and trans-hexahydrophthalazin-1(2H)-ones 7a,b with zinc powder in refluxing aqueous HCl (Scheme 4) resulted in the saturated isoindolones 8a,b in moderate yields (40-45%), in high stereoselectivity (>90% by HPLC), and the cis and trans anellations remaining unchanged in the course of the ringcontraction [9]. In the case of the N-phenyl-substituted derivative, no ring-contraction was observed under similar conditions.…”

Section: Acid-promoted Rearrangementsmentioning

confidence: 98%

Acid- and Base-Promoted Rearrangements of Cycloalkane-Fused Heterocycles

Csende¹,

Miklós²,

Porkoláb³

2010

COC

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“…We recently described several cyclocondensation reactions of 4-and 5-oxocarboxylic acids with amines 1 and bifunctional amino derivatives, such as diamines, amino-alcohols and amino-thiols. 2 Further studies of the reactivity of cis-and trans-cyclohexane-fused 4-oxocarboxylic acids with various dehydrating agents (H 2 SO 4 , PPA, H 3 PO 4 , AcCl, Ac 2 O, and DCC) led to formation of unsaturated lactones exclusively, instead of the expected saturated anthraquinone derivatives.…”

Section: Introductionmentioning

confidence: 99%

Comparative intramolecular dehydrative lactonization of 4-oxocarboxylic acids

Csende¹

2006

Arkivoc

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Reaction of 3-(p-toluoyl)propanoic acid, 1a (R = H) with refluxing acetic anhydride resulted quantitatively in 2, a β,γ-unsaturated γ-lactone, which was then converted into 3a, an α,β-unsaturated lactone by isomerization with triethylamine. The methyl-substituted compound 1b (R = Me), an analogue of 1a, afforded the 2(5H)-furanone 3b directly by heating with Ac 2 O. Similar reaction of the cycloalkane-containing oxocarboxylic acids (4,5) led in excellent yields to the fused furanones 6 and 7, while treatment of 2-formyl-, 2-acetyl-and 2-(p-toluoyl)benzoic acids (8a-c) with Ac 2 O gave the 3-acetoxy-1-(3H)-isobenzofuranones, 9a-c.

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Synthesis and Structural Study of New Saturated Isoindol-1-one Derivatives

Cited by 17 publications

References 0 publications

Depalladation Reactions of Iminoacyl- and 2-Acetylarylpalladium(II) Complexes

Depalladation Reactions of Iminoacyl- and 2-Acetylarylpalladium(II) Complexes

Acid- and Base-Promoted Rearrangements of Cycloalkane-Fused Heterocycles

Comparative intramolecular dehydrative lactonization of 4-oxocarboxylic acids

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