Synthese von<i>o</i>-Arylvinyl- und<i>o</i>-Heteroarylvinylphenolen

Franke, Albrecht; Frickel, Fritz; Schlecker, Rainer; Thieme, P.

doi:10.1055/s-1979-28807

Cited by 12 publications

(9 citation statements)

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“…When Wittig olefination of the azabicycle 6 was attempted using the benzyl phosphonium salt with n BuLi as the base, the reaction did not proceed and only starting material was recovered. However using a Horner–Wadsworth–Emmons modification24,25 with benzyl diethyl phosphonate and n BuLi as base gave the required styrene 8a in good yield (84 %). Due to the steric hindrance of the ester group only the ( E )‐substituted olefin 8a was formed.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis of AE and BE Ring Analogues of the Alkaloid Methyllycaconitine

et al. 2009

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The synthesis of AE and BE analogues of the alkaloid methyllycaconitine is reported. The analogues contain two key pharmacophores: a 2‐(2‐methylmaleimido)benzoate ester and a homocholine motif formed from a tertiary N‐(3‐phenylpropyl)amine incorporated into either a 3‐azabicyclo[3.3.1]nonane (AE) or octahydroquinoline (BE) ring system. An additional aromatic group is introduced into the AE bicyclic system using a Horner–Wadsworth–Emmons reaction. The BE analogues are synthesised by a one‐pot cyclisation using ethyl α‐(bromomethyl)acrylate, a primary amine and cyclohexanone leading to an efficient assembly of an octahydroquinoline ring system that mimics the BE‐rings of methyllycaconitine. In both the AE and BE analogues, the key 2‐(2‐methylsuccinimido)benzoate ester pharmacophore is introduced by esterification of the alcohol precursors with 2‐(2‐methylmaleimido)benzoic acid (10) under Steglich conditions followed by hydrogenation over palladium on charcoal.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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Section: Resultsmentioning

confidence: 99%

“…Melting points were determined on a Kofler hot‐stage apparatus and are uncorrected. 2‐(3‐methyl‐2,5‐dioxo‐2,5‐dihydropyrrol‐1‐yl)benzoic acid ( 10 )33 and the diethylphosphonates25 were prepared as reported.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of AE and BE Ring Analogues of the Alkaloid Methyllycaconitine

et al. 2009

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“…8‐Hydroxy[2.2](1,4)phenanthrenoparacyclophane (29b). a) trans ‐4‐(4‐Methoxystyryl)[2.2]paracyclophane (27b): By methods described in the literature 4‐methoxybenzaldehyde ( 23b ) was reduced to benzyl alcohol 24b ,28 and this was converted via the bromide 25b 29 to the phosphonate 26b 30. A solution of 26b (2.32 g, 9.00 mmol) in anhydrous THF (100 mL) was cooled to 0 °C under nitrogen.…”

Section: Methodsmentioning

confidence: 99%

On the Functionalization of [2.2](1,4)Phenanthrenoparacyclophane

2007

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Two routes for preparing functionalized [2.2](1,4)phenanthrenoparacyclophanes are described: either the parent system 2 is subjected to electrophilic substitution (bromination, Friedel-Crafts acylation, Rieche formylation: preparation of 5, 6, 7, 11 and 12) or the desired substituents are incorporated in the early stages of the synthesis by the preparation of the corresponding functionalized styryl paracyclophanes and their photocyclization to the respective phenanthrenocyclophanes. By these specific routes various bro-

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“…Ϫ Elemental analyses: Heraeus CHN-O-Rapid. Ϫ Precursors for the syntheses have already been reported in the literature and were prepared as described or according to literature procedures: ethyl 3,4-dimethylbenzoate [22] [23] , 3,4-dimethylbenzyl alcohol [24] [25] , 3,4-dimethylbenzyl chloride [26] , ethyl 3,5-dimethylbenzoate [22] [27] , 3,5-dimethylbenzyl alcohol [24] [28] , 3,5-dimethylbenzyl chloride [26] [29] , 2,3-dichlorobenzoyl chloride [30] [31] , 2,3-dichlorobenzyl alcohol [24] [32] , 2,3-dichlorobenzyl chloride [33] [34] , 2,5-dichlorobenzyl alcohol [24] [35] , 2,5-dichlorobenzyl chloride [33] [36] , 3,5-dichlorobenzyl alcohol [24] [33] , 3,5-dichlorobenzyl chloride [33] , 3-chloro-2-methylbenzyl alcohol [37] , 3-chloro-2-methylbenzyl chloride [26] [38] , 4-bromomethylbenzoic acid [39] , methyl 4-bromomethylbenzoate [39] , 2,5-dimethoxybenzyl alcohol [40] [41] , 2,5-dimethoxybenzyl chloride [41] , diethyl benzylphosphonates 2a [42] , 2b [43] , 2c [44] , 2d [44] [ 45] , 2e [46] , 2g [47] , 2h [43] , 2i [45] , 2k [45] , 2m …”

Section: Methodsmentioning

confidence: 99%

Synthesis, Structures and Topochemistry of 2-Monovinyl-Substituted 1,4-Benzoquinones

Irngartinger¹,

Stadler

1998

Eur. J. Org. Chem.

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In the course of topochemical investigations of substituted quinones the 2‐monovinyl‐substituted 1,4‐benzoquinones 1 were synthesized by electrochemical oxidation of the corresponding 1,4‐dimethoxybenzene derivatives 3 to the quinone bisketals 4 and subsequent hydrolysis. In solution, the aryl‐substituted vinylquinones 1a−1t underwent unexpected Diels‐Alder additions. The stereochemically unique course of the reaction was proved spectroscopically and by X‐ray structure analysis of the dimer 8k. As a basic requirement for the topochemical studies, the crystal structures of eight quinones 1 were determined by X‐ray diffraction. In the crystals of 1a, 1c, 1e, 1f, 1i and 1n with an α‐type packing arrangement, the vinylic double bonds have short contacts (< 4.4 Å) across a centre of symmetry. The quinone 1k crystallizes in a β arrangement with short distances (< 4.0 Å) between molecules related by translation and in a γ arrangement without suitable contacts. The crystals of all quinones 1 were irradiated with UV light to perform [2+2] cycloadditions. The photoreactive quinones dimerized exclusively at the vinylic double bonds, resulting in the corresponding cyclobutanes 9. Topochemically controlled the dimers 9a−9c, 9e, 9l−9n, 9q, 9r and 9u with molecular Ci symmetry were formed whereas the dimers 9k and 9t have Cs symmetry. The structures of the cyclobutanes were determined by spectroscopical investigations and in the case of 9b, 9e and 9r additionally by X‐ray analysis. Despite short contacts, crystals of 1f and 1i were photostable. This is probably because of insufficient lattice flexibility indicated by relatively high densities.

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Synthese vono-Arylvinyl- undo-Heteroarylvinylphenolen

Cited by 12 publications

References 0 publications

Synthesis of AE and BE Ring Analogues of the Alkaloid Methyllycaconitine

Synthesis of AE and BE Ring Analogues of the Alkaloid Methyllycaconitine

On the Functionalization of [2.2](1,4)Phenanthrenoparacyclophane

Synthesis, Structures and Topochemistry of 2-Monovinyl-Substituted 1,4-Benzoquinones

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