Chemistry of Phosphonium Ylides. Part 35. Reaction of Trimethyl Tinazide with Phosphonium Ylides. Synthesis of Antitumor Phosphanylidene Stannanyl Triazole and Triazene Compounds

Soher S. Maigali, Mansoura A.

Abstract

The reaction of 4-azidotrimethylstannane (1) with the nucleophilic active phosphacumulene ylides 2a-c, took place by 1,3-dipolar cycloaddition to give phosphanylidene triazole derivatives 3a-c. Furthermore, the reaction of the azide 1 with hexaphenylcarbodiphosphorane (4) behaves differently and afforded the corresponding phosphanylidene triazene 6 and triphenylphosphane. Treatment of the azide 1 with the stabilized phosphonium ylide, methoxycarbonylmethylenetriphenylphosphorane (8) afforded the triazole (10) along with triphenylphosphine oxide. The antitumor activity of compounds 3b and 3c was evaluated, in vitro against (breast: MCF 7 and liver: HEPG 2) human solid tumor cell lines. They showed values closed to that recorded by the reference drug Doxorubicin.