Chemistry of Phosphorus Ylides, Part 30. Reaction of Camphorquinone Derivatives with Active Phosphacumulenes and Stabilized Phosphonium Ylides

doi:10.21608/ejchem.2010.1223

Egypt. J. Chem.

2010

DOI: 10.21608/ejchem.2010.1223

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Chemistry of Phosphorus Ylides, Part 30. Reaction of Camphorquinone Derivatives with Active Phosphacumulenes and Stabilized Phosphonium Ylides

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Cited by 6 publications

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Chemistry of Phosphorus Ylides. Part 37. The Reaction of Phosphonium Ylides with Indoles and Naphthofurans. Synthesis of Phosphanylidenes, Pyrans, Cyclobutenes, and Pyridazine as Antitumor Agents

Maigali

El‐Hussieny

Soliman

2014

Journal of Heterocyclic Chem

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The reaction of the stabilized phosphonium ylides 2a, b with indolinones 1a, b and naphthofuranone 13 afforded the corresponding propylidene and ethylidene derivatives 4a-d and 14a, b. On the other hand, the active phosphacumulenes 5a, b react with compounds 4a-d by [4 + 2]-cycloaddition to give the stable phosphanylidene indole pyranones 6a-h. Although compounds 14a, b afforded the naphthofuropyrans 16a-d and triphenylphosphane. Moreover, the phosphallene ylide 7 react with compounds 4a-d and 14a, b to give phosphanylidenecyclobuteneindoline 9a-d and naphthalenones 18a, b, respectively. In addition, the naphthofuropyridazine 21 was obtained from the reaction of the hydrazone 19 and the phosphacumulene 5a. The antitumor activity of some of the new compounds was evaluated, in vitro, against colon and hepatocellular carcinoma cell lines. They showed values closed to that recorded by the reference drug Doxorubicin.

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Chemistry of Phosphorus Ylides. Part 37. The Reaction of Phosphonium Ylides with Indoles and Naphthofurans. Synthesis of Phosphanylidenes, Pyrans, Cyclobutenes, and Pyridazine as Antitumor Agents

Maigali

El‐Hussieny

Soliman

2014

Journal of Heterocyclic Chem

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Chemistry of phosphorus ylides. Part 38: Synthesis and anticancer activity of cyclobutane, oxaphosphetane, oxaphosphinine, azaphosphetidene, and pyridazine derivatives

et al. 2013

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Chemistry of phosphorus ylides 31: Reaction of azidocoumarin with active phosphonium ylides, synthesis and antitumour activities of chromenones

2013

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The reaction of 4-azidochromen-2-one (1) with the nucleophilic phosphacumulene ylides 2, 8, and 12 afforded the new heterocyclic triazoles, triazepines, aziridine, pyrrolone containing a coumarin moiety. Cycloaddition reactions took place first to give triazoline 3 and 9. The triazolines rearranged to the triazepines 4, 10, and 13 accompanied by elimination of triphenylphosphine leading to the phosphorus-free triazepines 5, 11, and moreover, aziridine 6 was produced via nitrogen extrusion from the triazoline 3, followed by ring expansion to the pyrrolone 7. On the other hand, the reaction of the azidocoumarin 1 with the phosphallene yield 15 behaves differently and afforded the triazine 17 and azetone 18. The antitumour activity of compounds 3, 4, 6, and 11 was evaluated, in vitro, against (breast: MCF-7 and liver: HPEG2) human solid tumour cell lines. They showed values closed to that recorded by the reference drug doxorubicin.

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Chemistry of Phosphorus Ylides, Part 30. Reaction of Camphorquinone Derivatives with Active Phosphacumulenes and Stabilized Phosphonium Ylides

Cited by 6 publications

References 18 publications

Chemistry of Phosphorus Ylides. Part 37. The Reaction of Phosphonium Ylides with Indoles and Naphthofurans. Synthesis of Phosphanylidenes, Pyrans, Cyclobutenes, and Pyridazine as Antitumor Agents

Chemistry of Phosphorus Ylides. Part 37. The Reaction of Phosphonium Ylides with Indoles and Naphthofurans. Synthesis of Phosphanylidenes, Pyrans, Cyclobutenes, and Pyridazine as Antitumor Agents

Chemistry of phosphorus ylides. Part 38: Synthesis and anticancer activity of cyclobutane, oxaphosphetane, oxaphosphinine, azaphosphetidene, and pyridazine derivatives

Chemistry of phosphorus ylides 31: Reaction of azidocoumarin with active phosphonium ylides, synthesis and antitumour activities of chromenones

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