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Михайловский, А. Г.; Dolzhenko, Anton V.; Syropyatov, B. Ya.; Shklyaev, Yu. V.; Вахрин, М. И.

doi:10.1023/a:1020816304323

Cited by 13 publications

(9 citation statements)

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“…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%

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: Allylboronation Reactionsmentioning

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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“…To a solution of compound Ia -Ic and Ie -Ig (1 g, about 0.3 mmole) in 100 ml of anhydrous ether was added LiAlH 4 (0.3 g) and the mixture was stirred for 3 h and allowed to stand for 12 h. To this mixture was carefully added dropwise 5 ml of water and the solution was carefully decanted from the Al(OH) 3 precipitate. The precipitate was washed with 20 ml ether on a Schott funnel.…”

Section: Experimental Chemical Partmentioning

confidence: 99%

Synthesis and anticoagulant activity of 1-aryl derivatives of tetrahydroisoquinolines

et al. 2006

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A series of 1-aryl-3,3-dimethyl-3,4-dihydroisoquinolines were obtained by three-component (one-pot) condensation of veratrole, isobutylene oxide, and aromatic nitriles and then reduced to the corresponding 1,2,3,4-tetrahydroisoquinolines. Hydrochlorides of the synthesized compounds were tested for anticoagulant activity.As is known, the group of 3,3-dimethyl-3,4-dihydroisoquinoline derivatives and some other types of partly hydrogenated isoquinolines contain compounds possessing antiaggregant and hypotensive properties [1 -11].The main goals of this study were (i) to use the threecomponent (one-pot) reaction discovered in [12,13] for the synthesis of 1-aryl-3,4-dihydroisoquinolines with various substituents at the aromatic ring and (ii) to evaluate the anticoagulant activity of these compounds and the corresponding reduced analogs (1,2,3,4-tetrahydroisoquinolines).

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“…Alkylation of 1 by iodomethane or iodoethane formed the corresponding ethers 2 and 3, which were used without further purification in the next step of the Ritter cyclocondensation. Use of hydrogen cyanide [6], acetonitrile [7], and homoveratryl nitrile instead of benzylcyanide [8], chloroacetonitrile [9], and 3-cyanocoumarin [10] as the nitrile component formed the corresponding 3,4-dihydroisoquinolines 4-8. By analogy, reaction of allylbenzenes 2 and 3 with cyanoacetic acid amide produced amides 9 and 10 [11].…”

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confidence: 99%

Synthesis of isoquinoline alkaloid derivatives from eugenol

et al. 2012

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547.913+547.94+547.833.3 E. S. Limanskii, and M. I. VakhrinAlkylation under phase-transfer catalysis conditions (18-crown-6/KOH) of eugenol was used for cyclocondensation with nitriles (Ritter reaction), the products of which were isoquinoline derivatives.Eugenol (1, 4-allyl-2-methoxyphenol) is the main constituent of essential oil from Syzygium aromaticum (Eugenia caryophyllata) (Myrtaceae), Camelia sasanqua (Theaceae), certain basil species (Ocimum) (Lamiaceae), and other plants [1,2].Various isoquinoline derivatives, many of which can be viewed as synthetic alkaloid analogs, were prepared earlier by cyclocondensation of nitriles with dialkylbenzylcarbinols (Ritter reaction) [3]. The capability for this type of cyclocondensation involving instead of a carbinol 3,4-dimethoxy-and 3,4-methylenedioxyallylbenzenes, which are very similar to eugenol, was demonstrated in classical seminal studies [4,5]. The goal of the present study was to use in analogous syntheses eugenol derivatives and nitriles that were verified by us earlier in reactions with carbinols.Syntheses with a protected phenol hydroxyl were carried out first. The studies showed that the eugenol hydroxyl can be alkylated practically quantitatively under phase-transfer catalysis conditions using 18-crown-6/KOH. Alkylation of 1 by iodomethane or iodoethane formed the corresponding ethers 2 and 3, which were used without further purification in the next step of the Ritter cyclocondensation. Use of hydrogen cyanide [6], acetonitrile [7], and homoveratryl nitrile instead of benzylcyanide [8], chloroacetonitrile [9], and 3-cyanocoumarin [10] as the nitrile component formed the corresponding 3,4-dihydroisoquinolines 4-8. By analogy, reaction of allylbenzenes 2 and 3 with cyanoacetic acid amide produced amides 9 and 10 [11]. The fact that the cyclization occurred without protecting the phenol hydroxyl was interesting. The reaction of eugenol with cyanoacetamide gave enaminoamide 11. Me H 8 5 4 1 a b MeO R 1 O NH Me H O NH 2 2, 3 4 -8 c c 9 -114: R 1 = Et, R 2 = H; 5: R 1 = R 2 = Me 6: R 1 = Me, R 2 = 3,4-dimethoxybenzyl; 7: R 1 = Me, R 2 = CH 2 Cl 8: R 1 = Me, R 2 = 3-coumarinyl; 2, 9: R 1 = Me; 3, 10: R 1 = Et; 11: R 1 = H a. R 1 I, 18-crown-6/KOH; b. R 2 CN; c. NCCH 2 C(O)NH 2

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Cited by 13 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 anticoagulant activity of 1-aryl derivatives of tetrahydroisoquinolines

Synthesis of isoquinoline alkaloid derivatives from eugenol

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