Synthesis of pyrrolo[2,1-a]isoquinolines

Shklyaev, V. S.; Aleksandrov, B. B.; Михайловский, А. Г.; Вахрин, М. И.

doi:10.1007/bf00475653

Cited by 6 publications

(8 citation statements)

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“…In a compound of the 56 type with a 1-ethoxycarbonyl group (R 1 = COOEt, R 2 = H) under analogous conditions the latter takes part, together with the C (2) =O group [16,50,52], in reaction with hydrazine hydrate, and the product 59 is formed [51]. …”

Section: Reactions With Hydrazines and Hydroxylaminementioning

confidence: 97%

“…Substituted tetrahydropyrrolo[1,2-a]isoquinoline-2,3-diones of type 56 [12,17,23,52] and their benzannelated analogs 83 [16,27,60] react with triallylborane at the C (2) =O group with the formation of the corresponding unsaturated alcohols 84 and 85 [60] …”

Section: Allylboronation Reactionsmentioning

confidence: 99%

“…The reaction of substituted 5,5-dimethyltetrahydropyrrolo[1,2-a]isoquinolinediones 56 [16,50,52] with hydrazine hydrate, N,N-dimethylhydrazine, phenylhydrazine, semicarbazide, and thiosemicarbazide boiled in ethanol takes place at the C (2) =O group with the formation of the corresponding derivatives 57 or (with favorable structural factors) 58 with an intramolecular hydrogen bond [50,51]. In a compound of the 56 type with a 1-ethoxycarbonyl group (R 1 = COOEt, R 2 = H) under analogous conditions the latter takes part, together with the C (2) =O group [16,50,52], in reaction with hydrazine hydrate, and the product 59 is formed [51].…”

Section: Reactions With Hydrazines and Hydroxylaminementioning

confidence: 99%

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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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Section: Reactions With Hydrazines and Hydroxylaminementioning

confidence: 97%

Section: Allylboronation Reactionsmentioning

confidence: 99%

Section: Reactions With Hydrazines and Hydroxylaminementioning

confidence: 99%

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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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“…Compound IIb was previously characterized in the form of hydroiodide [10]; we have also biologically tested a hydrochloride with m.p. = 189 -190~ The synthesis and properties of other compounds were previously described in [14] (compound IIla), [12] (lib-Ile, Va, Vb, Xla, XIb), [11] (VI, Vlla, VIIb), and [13] (VIIIa, VIIlb). (IIIb, IIIc).…”

Section: Experimental Chemical Partmentioning

confidence: 99%

Synthesis and study of antiaggregative and hypotensive activity of 3,3-dialkyl- isoquinoline azomethines and their derivatives

et al. 1999

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“…Monitoring of the purity of the compounds obtained was carried out by TLC on Silufol UV-254 plates in the system acetone-ethanol-chloroform (1:3:6), the starting materials and products being colored in the visible part of the spectrum. Compound 3 has been described in [13]. All of the compounds were recrystallized from acetonitrile.…”

mentioning

confidence: 99%

Azocoupling reaction of 1-benzyl-3,4-dihydroisoquinolines with diazonium salts and the properties of its products

Сурикова

Михайловский

Vikhareva

et al. 2008

Chem Heterocycl Comp

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Synthesis of pyrrolo[2,1-a]isoquinolines

Cited by 6 publications

References 1 publication

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)

Synthesis and study of antiaggregative and hypotensive activity of 3,3-dialkyl- isoquinoline azomethines and their derivatives

Azocoupling reaction of 1-benzyl-3,4-dihydroisoquinolines with diazonium salts and the properties of its products

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