Synthesis of Amines from Norbornane Series

Yatsynich, E. A.; Петров, Д. В.; Докичев, В. А.; Tomilov, Yu. V.

doi:10.1007/s11178-005-0313-9

Cited by 7 publications

(6 citation statements)

References 12 publications

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“…The use of a 4.6 fold molar excess of LiAlH 4 led to reduction of the ester function as well to give the 3-[1-adamantyl(hydroxyl)methyl]-5-hydroxymethyl-1H-pyrazole (8) in 68% yield. It should be noted that formation of products of hydrogenation of the pyrazole ring (pyrazolines or pyrazolidines) was not observed in any of the experiments.…”

Section: -Carboxylate Obtainedmentioning

confidence: 99%

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Synthesis and reactions of methyl 3-(1-adamantyl-carbonyl)-4,5-dihydro-1H-pyrazole-5-carboxylate

Lozhkin

Петров

Докичев

et al. 2009

Chem Heterocycl Comp

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The development of methods for preparing novel adamantane derivatives is a current problem since representatives of this class of compound have a broad spectrum of physiological activity (psychostimulating, immunostimulating, anticancer, analgesic) and are used in medical practice as antiviral, anti-parkinsonian, and other preparations [1][2][3][4]. It is known that adamantyl-substituted pyrazole shows high antibacterial activity and is of interest as a chemotherapeutic agent [2].The 1,3-dipolar cycloaddition of diazo derivatives to unsaturated compounds [5,6] shows promise in the synthesis of five membered nitrogen heterocycles and this opens up broad possibilities for preparing novel, practically important polyfunctional materials of different structure. This methodology was used by us in the case of the synthesis of 3-aminopyrrolidin-2-ones, dihydrooxazolines, and 1,3-propylenediamines of the norbornane series [7][8][9][10].With the aim of preparing compounds containing a nitrogen heterocycle and an adamantane fragment we have, for the first time, in this work studied the 1,3-dipolar cycloaddition of 1-(1-adamantyl)-2-diazoethanone (1) to methyl acrylate. On the basis of the methyl 3-(1-adamantylcarbonyl)-4,5-dihydro-1H-pyrazole-

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Section: -Carboxylate Obtainedmentioning

confidence: 99%

“…This methodology was used by us in the case of the synthesis of 3-aminopyrrolidin-2-ones, dihydrooxazolines, and 1,3-propylenediamines of the norbornane series [7][8][9][10].…”

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confidence: 99%

Synthesis and reactions of methyl 3-(1-adamantyl-carbonyl)-4,5-dihydro-1H-pyrazole-5-carboxylate

Lozhkin

Петров

Докичев

et al. 2009

Chem Heterocycl Comp

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“…One convenient method of preparation of 1,3-propylenediamines consists in the hydrogenation over Raney Ni under hydrogen pressure of alkyl-and aryl-substituted pyrazolines [9][10][11]. By this procedure only 1,3-propylenediamines with branched hydrocarbon chain were prepared [9][10][11].…”

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confidence: 99%

Catalytic synthesis of 1,3-propylenediamines

et al. 2011

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“…exo-2-Amino-exo-3-aminomethylnorbornane 1 was prepared by a known method [20]. Analgesic activity of compounds 3a,b and 6 was studied on 24 white, nonpedigree mice of weight 20-22 g using the acetic acid writhing test which was carried out by a single intraperitoneal introduction of a 0.75% solution of acetic acid based on a calculated 0.1 ml per 10 g of body weight.…”

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confidence: 99%

Synthesis of norbornane series tetra- and hexahydropyrimidines

Shafikova

Петров

Sapozhnikova

et al. 2009

Chem Heterocycl Comp

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Pyrimidine derivatives attract the attention of synthetic chemists and of pharmacologists thanks to their unique properties of low toxicity and broad spectrum of physiological activity (analgesic, immunotropic, anti-inflammatory, antiviral, hepatoprotective, antioxidant, and antiradical) [1-7]. Many compounds used in medical practice are close analogs of pyrimidine nucleosides. Work on the synthesis of novel compounds amongst this class is very actively pursued [8][9][10][11]. It is known that pyrrolidinones containing a condensed norbornane fragment have antiarrhythmic properties and norbornane series amines and their acyl derivatives show neurotropic, anti-inflammatory, antiglycemic, and other types of activity [12][13][14][15]. There is, however, no information in the literature regarding the synthesis and properties of norbornanes containing condensed exoorientated tetra-and hexahydropyrimidine structures at the 2, 3 position of the norbornane ring.This report concerns the targeted synthesis of 3,5-diazatricyclo[6.2.1.0 2,7 ]undecanes containing tetraand hexahydropyrimidine fragments in an exo position to a norbornane structure through study of the condensation reaction of exo-2-amino-exo-3-aminomethylnorbornane (1) with formaldehyde, acetaldehyde, benzaldehyde, salicylaldehyde, acetone, methylcyclopropyl ketone, cyclohexanone, and urea and with formic, acetic, and benzoic acids.The reaction of diamine 1 with an equimolar amount of formaldehyde, acetaldehyde, benzaldehyde, or salicylaldehyde occurs at room temperature with heating of the reaction mass and gives a hard to separate mixture of condensation products.

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Synthesis of Amines from Norbornane Series

Abstract: Synthetic procedure was developed for preparation of exo-oriented di-and tetraamines of the norbornane series by 1,3-dipolar cycloaddition to norbornene and norbornadiene of generated in situ diazomethane followed by reduction of arising pyrazolines catalyzed by Raney nickel.

Cited by 7 publications

References 12 publications

Synthesis and reactions of methyl 3-(1-adamantyl-carbonyl)-4,5-dihydro-1H-pyrazole-5-carboxylate

Synthesis and reactions of methyl 3-(1-adamantyl-carbonyl)-4,5-dihydro-1H-pyrazole-5-carboxylate

Catalytic synthesis of 1,3-propylenediamines

Synthesis of norbornane series tetra- and hexahydropyrimidines

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