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Kas’yan, A. O.; Golodaeva, E. A.; Tsygankov, Alexander V.; Kas’yan, L. I.

doi:10.1023/a:1022553832553

Cited by 14 publications

(14 citation statements)

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“…We previously reported on reactions of stereoisomeric amines 45a and 45b with 2-[1-(3,4-epoxycyclohex-1-en-1-yl)]-1,3-dioxolane (52) and methyl 3,4-epoxycyclohexane-1-carboxylate (53) (Scheme 20). Epoxy derivative 54 was used as nucleophile in reactions with oxiranes 50 and 51 [62,63]. Analysis of the spectral parameters showed conservation of the epoxynorbornane fragment in products 55 and 56 (Scheme 21).…”

Section: Synthesis Of Amino Alcohols From Bi-and Polycyclic Cage-likementioning

confidence: 99%

“…It was rationalized in terms of steric hindrances to attack by nucleophile from the rear (endo) side of the carbon skeleton according to the S N 2 mechanism. Compounds 57 and 58 were described in [63,64], and amino alcohol 59 was reported in [65]. These amino alcohols were synthesized under similar conditions, namely by stirring p-nitrophenyloxirane (50) with the corresponding amines in isopropyl alcohol at room temperature.…”

Section: Synthesis Of Amino Alcohols From Bi-and Polycyclic Cage-likementioning

confidence: 99%

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Cage-like amino alcohols. synthesis, reactions, and application

Kas’yan

Пальчиков

2010

Russ J Org Chem

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The review analyzes methods for the synthesis of amino alcohols containing cage-like norbornene, norbornane, and adamantane fragments. Such reactions of amino alcohols as selective functionalization of hydroxy and amino groups, as well as heterocyclizations with formation of nitrogen-and oxygen-containing heterocycles, are considered. Biological activity of cage-like amino alcohols and their derivatives and their use as ligands in catalytic asymmetric syntheses are discussed.

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Section: Synthesis Of Amino Alcohols From Bi-and Polycyclic Cage-likementioning

confidence: 99%

Section: Synthesis Of Amino Alcohols From Bi-and Polycyclic Cage-likementioning

confidence: 99%

Cage-like amino alcohols. synthesis, reactions, and application

Kas’yan

Пальчиков

2010

Russ J Org Chem

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“…The ether from the filtrate was evaporated, and the residue was distilled in a vacuum to give 20 g of V; bp 100oC (5 mm Hg), n D 20 = 1.4936, d 4 20 = 1.0836. Published data [2]: bp 72380oC (0.7 mm Hg).…”

Section: -(Prop-2-ynyloxycarbonyl)bicyclo[221]hept-5-ene Vmentioning

confidence: 99%

“…Thanks to their rigid framework structure, these compounds with fixed substituents are promising models for studying structure3property relationships [1]. Some norbornene derivatives exhibit analgetic, antiseptic, and antiphlogistic properties [2,3]. Of particular interest are acetylenic esters of norbornenecarboxylic acid.…”

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Synthesis and corrosion-protective properties of acetylenic esters of bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

Mamedov

2004

Russ J Appl Chem

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A procedure was developed for preparing acetylenic esters of bicyclo[2.2.1]hept-5-ene-2-carboxylic acid. The structures of the compounds were confirmed by IR and 1 H NMR spectroscopy. The Kovats indices of the compounds were determined, and their boiling points were estimated by gas3liquid chromatography. The protective properties of the esters against acid corrosion of steel were studied.Norbornene derivatives exhibit various useful properties. Thanks to their rigid framework structure, these compounds with fixed substituents are promising models for studying structure3property relationships [1]. Some norbornene derivatives exhibit analgetic, antiseptic, and antiphlogistic properties [2,3]. Of particular interest are acetylenic esters of norbornenecarboxylic acid. On the one hand, they have valuable properties themselves; on the other hand, they are promising as synthetic precursors of diverse valuable compounds owing to the combination of reactive norbornene and acetylenic fragments [4].The synthesis of propargyl norbornenecarboxylate by esterification of norbornenecarboxylic acid with propargyl alcohol in the presence of Brønsted acid catalysts was described in [5]. However, the yield (30%) and purity (88%) of the target product were poor.Proceeding with studies concerned with synthesis of acetylenic esters of norbornenecarboxylic acids [6 38], we developed a convenient synthetic route to these compounds and examined their protective properties against acid corrosion of metals. The compounds were prepared by reactions of bicyclo[2.2.1]hept-5-ene-2-carboxylic acid chloride I with acetylenic alcohols II!IV: II!IV I V !VIIwhere R 1 = R 2 = H (II, V); R 1 = Me, R 2 = H (III, VI); R 1 = Me, R 2 = CH=CH 2 (IV, VII).The reaction with primary alcohol II occurs at room temperature with heat liberation and is complete in 0.5 h. With tertiary alcohols III and IV, the reaction is less facile, and the corresponding esters VI and VII were obtained by heating at 80oC for 5 h. The yield of the target products was 90 396%.The structure of esters V3VII was confirmed by independent synthesis. First, we prepared acetylenic acrylates IX!XI by a reaction of acryloyl chloride with acetylenic alcohols II3IV. This was followed by the Diels3Alder addition of cyclopentadiene VII to acrylates IX!XI to obtain compounds V3VII:; CO 2 ÄCÄCÄCÄR 2 6 V!VII , Ä Ä g g g g R 1 R 1 + K S Q ? IX!XI VIII (2)where R 1 = R 2 = H (IX); R 1 = Me, R 2 = H (X); R 1 = Me, R 2 = CH=CH 2 (XI).The constants of compounds IV3VII prepared by both procedures are identical; they are listed in Table 1. The compositions and structures of the compounds were also confirmed by elemental analysis and by IR (Table 1) and 1 H NMR spectroscopy. The IR spectra of V3VII contain the stretching vibration bands (cm !1 ) of C=O (1730 31740), C3O (122531240) and C=C (2160 32165) groups. The band at 3290 cm !1 in the spectrum of V is characteristic of the =C3H bond. The stereoisomers of V and VII have similar IR spectra, with the absorption bands of the double bond in the norbornen...

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Reactions of p‐Nitrophenyloxirane with Amines Containing Fragments with Bicyclic Skeleton.

et al. 2003

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Reactions of p-Nitrophenyloxirane with Amines Containing Fragments withBicyclic Skeleton. -Reaction of p-nitrophenyloxirane (I) with several amines containing norbornane-or norbornene-bearing substituents (II) provides access to the corresponding p-nitrophenyl-substituted ethanolamines (III). Compound (IIIe) is obtained as a mixture of two diastereomers and this is proposed to result from steric hindrance at the tertiary nitrogen atom. Acylation and sulfonylation of some of the novel amino alcohols is carried out to furnish amides or sulfonamides, resp., in good yields. A screening of the biological activity of compound (IIIa) reveals that it possesses analgesic, anticonvulsant, tranquilizing and antiphlogistic activity and is more active than the parent amine (IIa). -(KAS'YAN, A. O.; GOLODAEVA, E. A.; TSYGANKOV, A. V.; KAS'YAN, L. I.; Russ.

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Untitled

Cited by 14 publications

References 3 publications

Cage-like amino alcohols. synthesis, reactions, and application

Cage-like amino alcohols. synthesis, reactions, and application

Synthesis and corrosion-protective properties of acetylenic esters of bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

Reactions of p‐Nitrophenyloxirane with Amines Containing Fragments with Bicyclic Skeleton.

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