1-Azabicyclo[3.2.0]heptane-3,4-diones (6). A Novel Method of Regio-controlled Synthesis of Functionalized Hydroindoles and Erythrinan Derivatives

Sano, Takehiro; Toda, Jun; Horiguchi, Yuji; Imafuku, K.; Tsuda, Yoshisuke

doi:10.3987/r-1981-09-1463

Cited by 13 publications

(8 citation statements)

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“…Their reactions with nucleophilic reagents, allylboronation, reduction, and thermal transformations are discussed.The chemistry of 2,3-dihydro-2,3-pyrrolediones condensed with azaheterocycles on the [a] side first evolved in the seventies, when the application of 2,3-dihydro-2,3-pyrroledione derivatives as synthetic blocks for the construction of alkaloid molecules was first demonstrated [1][2][3][4][5][6][7].It should be mentioned that up to the beginning of the nineties these annelated dihydropyrrolediones were studied almost exclusively as subjects for photoreduction and photocyclization or as dienophiles in DielsAlder reactions (for the production of intermediate compounds in the synthesis of alkaloids). A large part of these papers belong to certain groups of investigators [1][2][3][4][5].…”

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confidence: 99%

Synthesis and chemical transformations of 2,3-dihydropyrrole-2,3-diones annelated on the [a] side by azaheterocycles. (Review)

Mashevskaya

Масливец

2006

Chem Heterocycl Compd

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Data on methods for the synthesis of 2,3-dihydro-2,3-pyrrolediones condensed with azaheterocycles on the [a] side are reviewed. Their reactions with nucleophilic reagents, allylboronation, reduction, and thermal transformations are discussed.The chemistry of 2,3-dihydro-2,3-pyrrolediones condensed with azaheterocycles on the [a] side first evolved in the seventies, when the application of 2,3-dihydro-2,3-pyrroledione derivatives as synthetic blocks for the construction of alkaloid molecules was first demonstrated [1][2][3][4][5][6][7].It should be mentioned that up to the beginning of the nineties these annelated dihydropyrrolediones were studied almost exclusively as subjects for photoreduction and photocyclization or as dienophiles in DielsAlder reactions (for the production of intermediate compounds in the synthesis of alkaloids). A large part of these papers belong to certain groups of investigators [1][2][3][4][5]. Single reports on reactions with nucleophilic reagents, allylboronation, reduction, and thermal transformations of 2,3-dihydro-2,3-pyrrolediones annelated with azaheterocycles on the [a] side have only begun to appear comparatively recently. This region of their chemical behavior has been studied little in spite of the fact that they exhibit high reactivity toward various nucleophiles (particularly with the presence of several electron-withdrawing substituents in the rings) and generate imidoylketenes during thermolysis.In the present review we examine publications existing up to March, 2002, on methods for the production of dihydropyrrolediones condensed with azaheterocycles and their chemical transformations. The review does not include data on the chemistry of isatins and their aza analogs, which were described in [8], or data on the cycloaddition of these pyrrolediones, which have been discussed before [1][2][3][4][5][6][7][9][10][11] and were reviewed in [11].

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confidence: 99%

Synthesis and chemical transformations of 2,3-dihydropyrrole-2,3-diones annelated on the [a] side by azaheterocycles. (Review)

Mashevskaya

Масливец

2006

Chem Heterocycl Compd

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“…[1][2][3][4][5] Until the early nineties these annulated pyrrolediones were studied almost exclusively as subjects for photoreduction and photocyclisation, or as dienophiles in Diels-Alder reactions (for the production of intermediate compounds in the synthesis of alkaloids). A large number of these studies were performed by a certain groups of investigators.…”

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confidence: 99%

Reactions of fused pyrrole-2,3-diones with binucleophiles

Konovalova¹,

Shklyaev²,

Масливец³

2015

Arkivoc

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“…Tsuda found that 2-trimethylsiloxybutadiene adds readily and selectively to a particular heterocyclic class of enone-reminescent substrates possessing extended chromophores (ref. 24). Our investigations revealed a more general utility of this siloxy-substituted diene.…”

Section: A Rearrangements: Four Generations Of Oxadi-it-methane(odpmmentioning

confidence: 63%

Synthesis of natural products based on photochemical key transformations

Demuth¹

1986

Pure and Applied Chemistry

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-Three photochemical methods aiming primarily at syntheses of cyclopentanoid natural products are described: (A) The development and synthetic applications of four generations of tricyclooctanone-type key intermediates -all products of oxadi-ir-methane rearrangements -are reviewed. Most recent achievements are the total syntheses of (-)-5-oxosilphiperfol-6-ene and of (-)-coriolin. (B) The [2+2] photocycloaddition of 2-trimethylsiloxybutadiene to a number of standard enones proved to be quite a general reaction with appreciable yields. This finding is surprising since dienes in general are known to quench enone triplets efficiently and hence suppress chemical reactions. Both the high substrate concentrations, which can be employed in the present procedure, and the remarkable regio-and stereocontrol of the addition processes qualify this annulation as a valuable synthetic method. One photoproduct is the point of departure for an expedient assembly of the basic pentalenolactone skeleton. (C) Spirocyclic chiral 1,3-dioxenones, prepared in a one-step procedure, served for highly selective asymmetric [2+2] d.Mayo-type photocycloadditions with various olef ins. The value of this novel method is documented by an exploratory preparative example, a short synthesis of (+)-grandisol.

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1-Azabicyclo[3.2.0]heptane-3,4-diones (6). A Novel Method of Regio-controlled Synthesis of Functionalized Hydroindoles and Erythrinan Derivatives

Cited by 13 publications

References 0 publications

Synthesis and chemical transformations of 2,3-dihydropyrrole-2,3-diones annelated on the [a] side by azaheterocycles. (Review)

Synthesis and chemical transformations of 2,3-dihydropyrrole-2,3-diones annelated on the [a] side by azaheterocycles. (Review)

Reactions of fused pyrrole-2,3-diones with binucleophiles

Synthesis of natural products based on photochemical key transformations

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