A general approach to triphenylenes and azatriphenylenes: total synthesis of dehydrotylophorine and tylophorine

McIver, Andrew L.; Young, Douglas D.; Deiters, Alexander

doi:10.1039/b811068a

Cited by 74 publications

(48 citation statements)

References 54 publications

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“…Contemporary synthetic methods broadly use a cycloaddition reaction of hard to obtain alkenes or arylacetylenes with aromatic substrates catalyzed by transition metal salts [9,10]. Finally, the cyclocondensation of phenanthrenequinone with hydrazones of (hetero)aromatic carboxylic acid amides leads to the corresponding aryl- [11,12] and hetaryl-substituted [13] triazatriphenylenes.…”

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confidence: 99%

Preparation of Pyridyl-substituted Monoazatriphenylenes

Kopchuk

Zyryanov

Коvalev

et al. 2013

Chem Heterocycl Comp

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Azatriphenylene derivatives are of considerable interest due to their promising photophysical and coordinating properties [1] and to their presence in the composition of natural compounds [2,3]. Azatriphenylenes are important in inorganic biochemistry thanks to their use as intercalating ligands [4,5]. In addition, azatriphenylenes have shown promise as luminescent chemosensors of organic anions and nitroaromatic compounds [6].The most frequently used method for preparing azatriphenylenes is the Skraup synthesis [7,8] which demands the use of forcing conditions. Contemporary synthetic methods broadly use a cycloaddition reaction of hard to obtain alkenes or arylacetylenes with aromatic substrates catalyzed by transition metal salts [9,10]. Finally, the cyclocondensation of phenanthrenequinone with hydrazones of (hetero)aromatic carboxylic acid amides leads to the corresponding aryl- [11,12] and hetaryl-substituted [13] triazatriphenylenes.In this report, we propose an efficient method for the synthesis of cycloalkene-annelated derivatives of monoazatriphenylenes based on an aza-Diels-Alder reaction of the previously uncharacterized 3-(pyridin-2-yl)phenathro[9,10-e][1,2,4]triazine (1) [14] with 1-morpholinocycloalkenes. A method for preparing different pyridine derivatives through reaction of the corresponding mononuclear 1,2,4-triazines has been known for some time [15][16][17]. In our work, we have used this method for the first time in a single-stage synthesis of the poorly available pyridyl-substituted monoazatriphenylenes 2a,b.

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mentioning

confidence: 99%

Preparation of Pyridyl-substituted Monoazatriphenylenes

Kopchuk

Zyryanov

Коvalev

et al. 2013

Chem Heterocycl Comp

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“…Deiters group has developed an efficient, rapid and high-yielding method for the synthesis of triphenylenes using a microwave-mediated [2+2+2] cyclotrimerization reaction. [113] This has enabled the facile synthesis of several members of this important compound class. Moreover, the developed approach was adapted to the synthesis of azatriphenylenes, molecules which have been largely unexplored.…”

Section: Cobalt-catalyzed [2+2+2] Cycloadditionmentioning

confidence: 99%

Mono‐ and Polyazatriphenylene‐Based Ligands: An Updated Library of Synthetic Strategies (2001–2018)

et al. 2018

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This review surveys the most useful strategies for the synthesis of azatriphenylenes. Azatriphenylene derivatives are of considerable interest due to their promising photophysical and coordinating properties and to their presence in the composition of natural products. These scaffolds have shown ability as photoluminescent chemosensors for organic anions and nitroaromatic compounds. The straight‐forward construction of an azatriphenylene moiety from the easily available chemicals is desirable due to its tremendous use in the various branches of chemistry and material sciences. These target compounds can also be used as components of (metallo)intercalators (insertors) for biological studies as well as photoluminescent emitters. Here we report a review on the synthesis of these scaffolds employing different strategies such as cyclocondensation reaction, Friedel–Crafts reaction, Westphal condensation reaction, Chichibabin‐type condensation reaction, coupling reaction, intermolecular homocoupling‐cyclotrimerization reaction, cycloaddition reaction, Pomeranz–Fritsch cyclization and intramolecular cyclization reaction. In addition, a brief historical approach has also been discussed. This review will cover the synthetic routes to afford azatriphenylene derivatives broadly including mono‐, di‐, tri‐, tetra, and hexa‐azatriphenylenes. As a consequence, this review will contribute ample and updated information on the synthesis of this class of compounds.

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“…Notably, this basic strategy for pyridine synthesis, that employs a symmetric diyne and a nitrile, has been adopted for the synthesis of other alkaloid targets. 159 …”

Section: Metallacycle-mediated Cross-coupling By [2+2+2]mentioning

confidence: 99%