Chemo‐Selective Synthesis of Tetrazole‐Containing Cyclopentenyl Phosphanylidene Dicarboxylates

Abstract

A chemo-selective clean reaction between triphenylphosphine (TPP) and dialkyl acetylenedicarboxylates (DAAD) in the presence of synthesized alkyl 3-phenyl-2-(1H-tetrazol-5-yl)acrylates for generation of the 3-alkyl 1-alkyl 4-oxo-2-phenyl-3-(1Htetrazol-5-yl)-5-(triphenyl-λ 5 -phosphanylidene)cyclopent-1-ene-1,3-dicarboxylates is described. 2 3 4 5 6 7 8

Synthesis of novel organophosphorus compounds via reaction of substituted 2-oxoindoline-3-ylidene with acetylenic diesters and triphenylphosphine or triphenyl phosphite

“…In our previous study, we observed that the vinyl phosphonium zwitterionic intermediate (A) reacted with the conjugated C-C double bond instead of the NH of tetrazole, and the reaction proceeded via a Michael addition to produce the final product 8 (Fig. 6) 30 . However, in the current study, neither the, NH of tetrazole nor the conjugated C-C double bond have any reaction with the vinyl phosphonium zwitterion.…”

“…1). Herein, according to our investigations [27][28][29][30] , due to the importance of organophosphorus compounds and isatin cores, we describe the synthesis of functionalized 2-oxoindoline-3-ylidene containing novel organophosphorus compounds. Therefore, we have performed a facile one-pot reaction between 2-oxoindoline-3-ylidene derivatives and triphenyphosphine or triphenyl phosphite in the presence of acetylenic esters.…”

“…Then, compound 3 reacts with sodium azide in ethanol at 70 °C to obtain ethyl 2-(2-oxoindolin-3-ylidene)-2-(2H-tetrazol-5-yl)acetate 4 following the previous procedure (Fig. 3) 30 .…”