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1,2-Bis(2-pyridyl)ethane-1,2-dione was allowed to react with different phosphorus nucleophiles. Treatment of the 1,2-bis(2-pyridyl)ethane-1,2-dione with the active phosphacumulene ylides, (N-phenyl...

The reaction of 4-azido-2-oxo-2H-chromene-3-carbaldehyde with the active nucleophilic phosphacumulenes yielded the corresponding phosphanylidene-aziridines and chromeno-pyrolo-triazoles. On the other hand, the reaction of the allylic phosphonium ylide, hexaphenylcarbodiphosphorane with the azido compound, was also undertaken. In this case, the phosphanylidene-chromeno-triazinone was obtained. Further assessment of these new compounds against (breast: MCF-7 and liver: HPEG2) human solid tumor cell lines is necessary.

A comparative study between the reactions of active phosphacumulenes and stabilized phosphonium ylides on some diazo compounds have been performed. A number of substituted phosphanylidene spiro pyrazoles have been synthesized from the reaction of the active phosphacumulenes and the diazo derivatives. On the other hand, treatment of the diazo substrates with the stabilized phosphonium ylides led to the formation of the corresponding ylidenes and diazenyl phosphanylidenes. The antimicrobial activities for the new compounds are also reported.

The reaction of the stabilized phosphonium ylides 2a, 2b with indolinones 1a, 1b and naphthofuranone 13 afforded the corresponding propylidene and ethylidene derivatives 4a, 4b, 4c, 4d and 14a, 14b. On the other hand, the active phosphacumulenes 5a, 5b react with compounds 4a, 4b, 4c, 4d by [4 + 2]-cycloaddition to give the stable phosphanylidene indole pyranones 6a, 6b, 6c, 6d, 6e, 6f, 6g, 6h. Although compounds 14a, 14b afforded the naphthofuropyrans 16a, 16b, 16c, 16d and triphenylphosphane. Moreover, the phosphallene ylide 7 react with compounds 4a, 4b, 4c, 4d and 14a, 14b to give phosphanylidenecyclobuteneindoline 9a, 9b, 9c, 9d and naphthalenones 18a, 18b, 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.

The stabilized alkylidenephosphoranes namely, acetyl-, benzoyl-, methoxycarbonyl-, and ethoxycarbonyl-methylenetriphenylphosphorane react with 2-hydroxyisoindole-1,3-(2H)dione to give the corresponding isoindoline-ylidenes, along with triphenylphosphane oxide. On the other hand, the reaction of active phosphacumulenes, (N-phenyliminovinylidene)-, and (2-oxovinylidene)-triphenylphosphorane with hydroxyisoindole-, isoindoline-, and indane-1,3-dione afforded phosphanylidenecyclobutylidenes derivatives, together with triphenylphosphane oxide. Mechanisms accounting for the formation of the new products are discussed. The antimicrobial activities for the new compounds are also reported. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.

The reaction of nucleophilic phosphacumulene and phosphallene ylides with different chromenone derivatives was investigated. Heterocycles and carbocycles of various ring sizes and heteroatom patterns such as pyrano-, oxaphosphino-, cyclopenta-, phosphoranylidene cyclobutane-, and phospholo-chromenones were obtained. The antitumor (breast and liver) properties of some new compounds were performed in vitro. Some of these compounds were more potent than the comparative standard.