One-Pot Synthesis of New Unsymmetrical b-Heteroaryl-o-divinylbenzenes

Šindler‐Kulyk, Marija; Stiplošek, Z.; Vojnovic, D.; Metelko, Biserka; Marinić, Željko

doi:10.3987/com-91-5846

Cited by 34 publications

(15 citation statements)

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“…[39] They were obtained in moderate-to-good yields (49-85 %) as mixtures of cis,cis, cis,trans and trans,trans isomers with the cis,trans isomers being dominant. The isomers of 9-11 were separated by a combination of column chromatography and thinlayer chromatography on silica gel and identified spectroscopically.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Photochemistry of β,β′‐Di(2‐furyl)‐Substituted o‐Divinylbenzenes: Intra‐ and/or Intermolecular Cycloaddition as an Effect of Annelation

Škorić

Basarić

Marinić

et al. 2004

Chemistry A European J

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New heteroaryl-substituted o-divinylbenzenes, 2,2'-(1,2-phenylenedivinylene)difuran (9), 2,2'-(1,2-phenylenedivinylene)bisbenzo[b]furan (10), and 2,2'-(1,2-phenylenedivinylene)bisnaphtho[2,1-b]furan (11), were prepared and irradiated at various concentrations; intramolecular photocycloaddition and intermolecular [2+2] twofold photoaddition reactions took place to give bicyclo[3.2.1]octadiene derivatives 12-14 and cyclophane derivatives 15-17, respectively. Compound 11 was the most selective of these o-divinylbenzenes, which, owing to pi-pi intra- or intermolecular complexation, gave only the exo-bicyclo[3.2.1]octadiene derivative 14 at low concentrations, and only the cyclophane derivative 17 at high concentrations.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Photochemistry of β,β′‐Di(2‐furyl)‐Substituted o‐Divinylbenzenes: Intra‐ and/or Intermolecular Cycloaddition as an Effect of Annelation

Škorić

Basarić

Marinić

et al. 2004

Chemistry A European J

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“…[19] Derivatives that have been investigated so far have been those with phenyl and 2-furyl substituents (Scheme 2). The Wittig reaction was conducted according to the "onepot" procedure described in a previous paper [20] and gave a mixture of isomers (1a-c E,Z/E,E = 3:4 and 1d E,Z/E,E = 1:1), in moderate to good yields (44-71 %). Desired derivatives with the benzobicyclo[3.2.1]octadiene skeleton (G) as well as polycyclic products H were synthesized, purified, and described (Scheme 2).…”

Section: Introductionmentioning

confidence: 99%

Formation of Polycyclic Skeletons by Photochemical Transformations of Pyridyl‐ and Thienylbutadiene Derivatives

et al. 2017

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In order to study the influence of heterocyclic nuclei on the photochemical behavior of conjugated butadiene systems, novel butadiene derivatives E,Z‐ and E,E‐2/3‐[4‐(2‐vinylphenyl)buta‐1,3‐dienyl]thiophene as well as E,Z‐ and E,E‐3/4‐[4‐(2‐vinylphenyl)buta‐1,3‐dienyl]pyridine have been synthesized. The Wittig reaction was utilized in a two‐step reaction course. During the first Wittig reaction, the corresponding aldehydes, namely 2/3‐thiophenecarboxaldehyde and 3/4‐pyridinecarboxaldehyde, reacted with formylmethylenetriphenylphosphorane to give the corresponding acrylaldehydes, which reacted with the diphosphonium salt of α,α′‐o‐xylenedibromide in the second Wittig reaction to give new butadiene derivatives. These butadiene derivatives afforded, by photochemical intramolecular cycloaddition, new fused tricyclic as well as tetracyclic derivatives. For the first time, a study of efficiency was conducted where the efficiency of intramolecular cycloaddition of these heterocyclic butadiene derivatives was investigated by simultaneous use of ferrioxalate and valerophenone actinometers.

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“…Our recent research on the intramolecular photochemical reactions of conjugated thiophene derivatives 1,2 continues the work on furan [3][4][5][6][7][8][9][10] and pyrrole [11][12][13][14][15][16] derivatives of o-divinylbenzenes. Dithiophene derivatives 1, 2 react differently 2 in comparison to previously studied difuran 3 8 and dipyrrole 4 12 derivatives ( Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Photochemical and Thermal Transformations of Thiophene o-Distyrylbenzene Analogues in Acidic Media

Vuk¹,

Marinić²,

Molčanov³

et al. 2012

Croat. Chem. Acta

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Abstract. Intramolecular photochemical reactions of thiophene analogues of o-distyrylbenzene, 2,2'-(o-phenylenedivinylene)dithiophenes (1a,b), 3,3'-(o-phenylenedivinylene)dithiophene (2a) and 3,3'-(o-phenylenedivinylene)dibenzothiophene (2b), were studied in acidic media at low concentrations. A 1,6-and 1,5-ring closure of hexatriene system leading to dihydronaphthalene or indene derivatives, respectively, was observed. (doi: 10.5562/cca2120)

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One-Pot Synthesis of New Unsymmetrical b-Heteroaryl-o-divinylbenzenes

Cited by 34 publications

References 0 publications

Synthesis and Photochemistry of β,β′‐Di(2‐furyl)‐Substituted o‐Divinylbenzenes: Intra‐ and/or Intermolecular Cycloaddition as an Effect of Annelation

Synthesis and Photochemistry of β,β′‐Di(2‐furyl)‐Substituted o‐Divinylbenzenes: Intra‐ and/or Intermolecular Cycloaddition as an Effect of Annelation

Formation of Polycyclic Skeletons by Photochemical Transformations of Pyridyl‐ and Thienylbutadiene Derivatives

Photochemical and Thermal Transformations of Thiophene o-Distyrylbenzene Analogues in Acidic Media

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