Synthesis of tetrazole-containing cyclopentenyl phosphanylidene dicarboxylates

Organophosphorus compounds have a special place in the synthetic chemistry.1,2 Over the past decade, because of the nucleophilic property of triphenyphosphine, use of it in the presence of electron deficient substrates such as acetylenic esters has been gained more attentions for the synthesis of new carbocyclic and heterocyclic scaffolds.3,4 Synthesis of highly functionalized carbocycles is interesting and important for industrial and biological sciences.5 Herein, we report new chemo-selective reaction of triphenylphosphine and alkyl 3-phenyl-2-(1H-tetrazol-5-yl)acrylates 3 in the presence of dialkyl acetylenedicarboxylates 4 to produce tetrazole containing of triphenylphosphanylidene cyclopentene dicarboxylates 5 (Fig. 1). All synthesized compounds are stable solids whose structures were determined on the basis oftheir mass spectrum, 1H and 13C NMR and IR spectroscopic data

Keywords:

Alkyl 3-phenyl-2-(1H-tetrazol-5-yl)acrylates , triphenylphosphine , Acetylenic diesters , Tetrazole , Triphenylphosphanylidene cyclopentene dicarboxylate