6(5<i>H</i>)‐phenanthridinones. II. Preparation of substituted 6(5<i>h</i>)‐phenanthridinones from 9‐oxofluorenes

Pan, Hsi-Lung; Fletcher, T. Lloyd

doi:10.1002/jhet.5570070210

Cited by 10 publications

(1 citation statement)

References 10 publications

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“…Owing to the many structural derivatives of phenanthridines [ 11 ], their synthesis has been known since the beginning of the 20th century [ 12 ]. There are many classical methods available, e.g., via the Schmidt reaction [ 13 , 14 , 15 , 16 ], the Ullmann reaction [ 17 ], and the Beckmann rearrangement reaction [ 18 , 19 ], dienone-phenol rearrangement [ 20 ], and intramolecular rearrangement reaction [ 21 ]. In addition, phenanthridinones can be constructed through dichromate oxidation [ 22 ], internal cyclisation of a benzyne intermediate [ 23 , 24 , 25 ], and other conventional methods [ 26 , 27 ].…”

Section: Introductionmentioning

confidence: 99%

Synthetic Strategies in the Preparation of Phenanthridinones

et al. 2021

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Phenanthridinones are important heterocyclic frameworks present in a variety of complex natural products, pharmaceuticals and displaying wide range of pharmacological actions. Its structural importance has evoked a great deal of interest in the domains of organic synthesis and medicinal chemistry to develop new synthetic methodologies, as well as novel compounds of pharmaceutical interest. This review focuses on the synthesis of phenanthridinone scaffolds by employing aryl-aryl, N-aryl, and biaryl coupling reactions, decarboxylative amidations, and photocatalyzed reactions.

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Section: Introductionmentioning

confidence: 99%

Synthetic Strategies in the Preparation of Phenanthridinones

et al. 2021

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The Schmidt Reaction

et al. 2012

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The classical form of the Schmidt reaction involves the reaction of a carbon‐centered electrophile with hydrazoic acid with loss of nitrogen, usually with a rearrangement that forms a new carbon‐nitrogen bond. Although the conversion of a ketone into an amide is the most commonly used variation, mechanistically related versions utilize an aldehyde, acid, or a carbocation generated from an alkene or alcohol as the electrophilic component. In recent years, the definition of the Schmidt reaction has been modified to include analogous reactions in which the hydrazoic acid is replaced by an alkyl azide, promoted by Lewis acids. The use of an alkyl azide uniquely permits the formulation of intramolecular Schmidt reactions of the azide with a carbonyl or carbocationic electrophile.

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Synthese des Narciprimins und verwandter Verbindungen

Mondon

Krohn

1972

Chem. Ber.

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Synthesis of Narciprimine and Related Compounds *) As a model reaction for the synthesis of narciprimine (1) the formation of unsymmetrically substituted phenanthridones by photocyclisation of benzanilides is investigated. For example, arolycoricidine (2) is easily accessible from 18 via 20. Narciprimine, however, can be obtained only by irradiation of a bromine containing precursor as 28. I n this reaction, the dibenzylether 36 is formed which can be debenzylated partially or completely to give 35 and 1, respectively. 36 is a convenient starting material for the synthesis of the new compound N-methylnarciprimine (40). The N-methylphenanthridone derivative 46, most conveniently prepared by photocyclisation of 45, yields permethyl-isonarciprimine (3) and permethylisoarolycoricidine (4) in only a few steps. In a modified Pschorr synthesis, besides 46 the novel spirocyclohexadienyl dimers 51a and c were formed.Piozzi und Mitarbb.3) berichteten 1968 uber das Mitosegift Narciclasin aus Narzissenzwiebeln. Sie fanden als Begleitstoff das inaktive Narciprimin, das auch kiinstlich durch Wasserabspaltung erhalten werden kann". Im gleichen Jahr erschien eine Arbeit von Okamoto und Mitarbb.5) uber das Mitosegift Lycoricidinol aus den Zwiebeln von Lycoris radiata. Auch diese Verbindung spaltet unter Einwirkung von Saure Wasser ab zum Arolycoricidinol. Wir konnten durch direkten Vergleich die Annahmes) bestatigen I), dalj Narciclasin und Lycoricidinol -und damit auch deren Folgeprodukte iibereinstimmen6).

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6(5H)‐phenanthridinones. II. Preparation of substituted 6(5h)‐phenanthridinones from 9‐oxofluorenes

Cited by 10 publications

References 10 publications

Synthetic Strategies in the Preparation of Phenanthridinones

Synthetic Strategies in the Preparation of Phenanthridinones

The Schmidt Reaction

Synthese des Narciprimins und verwandter Verbindungen

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