Ungesättigte Reste in chemischer und pharmakologischer Beziehung (III.)

Braun, Julius v.; Lemke, Georg

doi:10.1002/cber.19220551022

Cited by 19 publications

(7 citation statements)

References 15 publications

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“…To derive the systems 4( 3 ) and 4( 5 ) we employed a four-component cyclization reaction of the di(lithium) salt of 1,4-di(ethynyl)benzene ( 11 ) and the corresponding α,ω-dithiocyanatoalkanes 12( n ) ( n = 3, 5) following previously published procedures. ,, The dithiocyanatoalkanes used in this paper have been described in the literature . The reaction was carried out in anhydrous THF under argon atmosphere at −40 °C.…”

Section: Resultsmentioning

confidence: 99%

Macrocyclic Cyclophanes with Two and Three α,ω-Dichalcogena-1,4-diethynylaryl Units: Syntheses and Structural Properties

et al. 2008

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By means of four- and six-component cyclization reaction various cyclophanes were synthesized. The components were the di(lithium) salts of 1,4-di(ethynyl)benzene (11), 4,4'-di(ethynyl)biphenyl (13), 1,4-di(ethynyl)-2,5-di(n-hexyl)benzene (18), and 1,4-di(ethynyl)-2,5-di(n-propyl)benzene (19). These building blocks were reacted with alpha,omega-dithiocyanato-n-alkanes and alpha,omega-diselenocyanato-n-alkanes with n = 3-6. In the case of 10 also 1,1'-di(2-thiocyanatoethyl)cyclohexane (24) was reacted to afford a cyclophane comprising three subunits of 11. From most of the resulting macrocyclic cyclophanes (4(n) (n = 3, 5), 5, 6, 7(n) , 8(n) (n = 3-6), 9(n) (n = 3, 5), and 10), we were able to grow single crystals. The X-ray analysis of 4(3), 7(3), 8(3), 8(4), 6, 7(5), and 8(5) revealed close contacts between the chalcogen atoms. These chalcogen-chalcogen interactions impose a ribbon-shape arrangement of molecules in 4(3) and a mutual crossing of two perdendicular planes built of 8(4) molecules. For 4(3) we found a close contact (3.28 A) between the pi planes of two neighboring C6H4 rings of different molecules, whereas in 8(4) such a close contact (3.74 A) was due to an intermolecular interaction. Tubular stacking of the macrocyclic rings was found for 7(5) and 8(5) caused by a ladder-type intermolecular chalcogen-chalcogen interaction.

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Section: Resultsmentioning

confidence: 99%

Macrocyclic Cyclophanes with Two and Three α,ω-Dichalcogena-1,4-diethynylaryl Units: Syntheses and Structural Properties

et al. 2008

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“…Ϫ Elemental analyses were carried out by the Mikroanalytisches Laboratorium der Universität Heidelberg. Ϫ Trimethylsilylacetylene (9) [19] and the dithiocyanatoalkanes 12, [10] 13, [11] 14, [12] 15, [13] 16, [14] 17 [14] were prepared according to literature methods. Dithiocyanatomethane (11) was purchased from Acros and recrystallized from ethanol before use.…”

Section: Methodsmentioning

confidence: 99%

Syntheses and Structural Properties of Cyclic Tetrathiadiynes

et al. 2000

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“…62 ). First dimers of this type were reported in the 1920’s and used 1,4- -but-2-ene and butane linkers in DHQN-216 and DHQN-217a , respectively [ 143 ]. Cowman obtained a series of dimers with linkers of 4-14 carbon atoms DHQN-217a – f as well as with piperazine-derived linker DHQN-218 [ 144 ].…”

Section: Quinoline Ringmentioning

confidence: 99%

Dimeric Cinchona alkaloids

Boratyński

2015

Mol Divers

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Nature is full of dimeric alkaloids of various types from many plant families, some of them with interesting biological properties. However, dimeric Cinchona alkaloids were not isolated from any species but were products of designed partial chemical synthesis. Although the Cinchona bark is amongst the sources of oldest efficient medicines, the synthetic dimers found most use in the field of asymmetric synthesis. Prominent examples include the Sharpless dihydroxylation and aminohydroxylation ligands, and dimeric phase transfer catalysts. In this article the syntheses of Cinchona alkaloid dimers and oligomers are reviewed, and their structure and applications are outlined. Various synthetic routes exploit reactivity of the alkaloids at the central 9-hydroxyl group, quinuclidine, and quinoline rings, as well as 3-vinyl group. This availability of reactive sites, in combination with a plethora of linker molecules, contributes to the diversity of the products obtained.

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Ungesättigte Reste in chemischer und pharmakologischer Beziehung (III.)

Cited by 19 publications

References 15 publications

Macrocyclic Cyclophanes with Two and Three α,ω-Dichalcogena-1,4-diethynylaryl Units: Syntheses and Structural Properties

Macrocyclic Cyclophanes with Two and Three α,ω-Dichalcogena-1,4-diethynylaryl Units: Syntheses and Structural Properties

Syntheses and Structural Properties of Cyclic Tetrathiadiynes

Dimeric Cinchona alkaloids

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