A Detailed Investigation of the Reaction of 5,9-Diphenylbenz[a]azulene with Dialkyl Acetylenedicarboxylates Leading to Dialkyl 8,12-Diphenylbenzo[a]heptalene-6,7-dicarboxylates

Linden, Anthony; Meyer, Markus; Mohler, Peter; Rippert, Andreas Johannes; Hansen, Hans‐Jürǵen

doi:10.1002/(sici)1522-2675(19991215)82:12<2274::aid-hlca2274>3.0.co;2-9

Cited by 12 publications

(5 citation statements)

References 18 publications

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“…[107][108][109][110][111] Ninhydrin was used in the design and synthesis of various frameworks, both carbocyclic [112][113][114][115][116][117][118][119] and heterocyclic.…”

Section: -10mentioning

confidence: 99%

Ninhydrin in synthesis of heterocyclic compounds

Ziarani¹,

Lashgari²,

Azimian³

et al. 2015

Arkivoc

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Ninhydrin has been utilized in many heterocyclic preparations and considered as an important building block in organic synthesis. There is a wide range of reactions that include ninhydrin in the synthesis of heterocyclic compounds. This review highlights the advances in the use of ninhydrin as starting material in the synthesis of various organic compounds and drugs in a fully comprehensive way, from its first isolation in 1910 to the end of 2013. There is also a diversity of multi-component reactions of ninhydrin and we highlight the recent reports in this review.

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“…[107][108][109][110][111] Ninhydrin was used in the design and synthesis of various frameworks, both carbocyclic [112][113][114][115][116][117][118][119] and heterocyclic.…”

Section: -10mentioning

confidence: 99%

Ninhydrin in synthesis of heterocyclic compounds

Ziarani¹,

Lashgari²,

Azimian³

et al. 2015

Arkivoc

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“…However, when azulenes are exposed to ADM at 30° and at pressures of 7 kbar, the primary adducts of type A can be isolated and characterized [9] [10]. The solvent dependence of their transformation into heptalene-4,5-dicarboxylates indicates that the C(3)-C(3a) bond is cleaved heterolytically, followed by formation of 2aH-cyclobuta-[c]azulene-1,2-dicarboxylates, which then ring-opens to the observed heptalene-4,5-dicarboxylates of type D [10] [11].…”

Section: Azulenes and Acetylenedicarboxylates React Under Acid Catalymentioning

confidence: 99%

Excursion to the World of Heptacyclic Compounds Made of Azulenes and Acetylenedicarboxylates

Chen

Lehto

Uebelhart

et al. 2015

Helvetica Chimica Acta

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Azulenes and acetylenedicarboxylates react under acid catalysis (Brønsted or Lewis) and form (2aRS,8aSR)-2a,8a-dihydrocyclopenta[cd]azulene-1,2-dicarboxylates as intermediate products, which then dimerize by central bond-formation between C(2a1) and C(2'a1) and various peripheral C,C'-atoms of the dihydroazulene fragments, depending on the substituents present. The reactions are often accompanied by the formation of side-products, such as 2-(azulen-1-yl)fumarates and -maleates and others caused by H-shifts of the primary intermediates. H-Shifts between the two tetrahydrocyclopenta[ cd]azulene parts of the heptacyclic structures were also found.

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“…Benz[ a ]azulene, a structural isomer of anthracene, is one of the polycyclic aromatic compounds, which has also been of much interest in terms of its structural and optical properties . In this regard, several research groups have reported the preparation of benz[ a ]azulenes and their derivatives for a long time, but the synthetic method for the parent compound is still limited (Scheme ). To the best of our knowledge, the synthesis of the parent benz[ a ]azulene has first been achieved in 1948 by Plattner et al and Treibs, independently, in a similar manner, i.e., the reaction of fluorene with ethyl diazoacetate, but the yield of products was not available in the literature.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Reactivity, and Properties of Benz[a]azulenes via the [8 + 2] Cycloaddition of 2H-Cyclohepta[b]furan-2-ones with an Enamine

et al. 2022

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Starting with the reaction of 2H-cyclohepta[b]furan-2-ones with an enamine, which was prepared from 4-tert-butylcyclohexanone and pyrrolidine, benz[a]azulenes having both formyl and tert-butyl groups were obtained in the three-step sequence. Subsequently, both the formyl and tert-butyl groups were eliminated by heating the benz[a]azulene derivatives in 100% H3PO4 to give benz[a]azulenes without these substituents in high yields. In terms of product yield, this method is the best one ever reported for the synthesis of the parent benz[a]azulene so far. The conversion of the benz[a]azulene derivatives with a formyl group into cyclohept[a]acenaphthylen-3-one derivatives was also investigated via Knoevenagel condensation with dimethyl malonate, followed by Brønsted acid-mediated intramolecular cyclization. The structural features including the bond alternation in the benz[a]azulene derivatives were revealed by NMR studies, NICS calculations, and a single-crystal X-ray structural analysis. The optical and electrochemical properties of a series of benz[a]azulene derivatives were evaluated by UV/Vis, fluorescence spectroscopy, and voltammetry experiments. As a result, we found that some benz[a]azulene derivatives showed remarkable luminescence in acidic media. In addition, the benz[a]azulene derivatives with the electron-withdrawing group and cyclohept[a]acenaphthylen-3-one derivative displayed good reversibility in the spectral changes under the electrochemical redox conditions.

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A Detailed Investigation of the Reaction of 5,9-Diphenylbenz[a]azulene with Dialkyl Acetylenedicarboxylates Leading to Dialkyl 8,12-Diphenylbenzo[a]heptalene-6,7-dicarboxylates

Cited by 12 publications

References 18 publications

Ninhydrin in synthesis of heterocyclic compounds

Ninhydrin in synthesis of heterocyclic compounds

Excursion to the World of Heptacyclic Compounds Made of Azulenes and Acetylenedicarboxylates

Synthesis, Reactivity, and Properties of Benz[a]azulenes via the [8 + 2] Cycloaddition of 2H-Cyclohepta[b]furan-2-ones with an Enamine

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