Regioselective addition of alkyl phosphites on 6-(aryliminomethyl)-furobenzopyran-5-one derivatives

Ibrahim, Nabila M.; Magd-El-Din, Asmaa A.; El-All, Amira S. Abd; Al-Amrousi, Eman F.; Yosef, Hisham Abdallah A.

doi:10.7123/01.EPJ.0000421666.94096.f5

Regioselective addition of alkyl phosphites on 6-(aryliminomethyl)-furobenzopyran-5-one derivatives

Authors

10.7123/01.EPJ.0000421666.94096.f5

Abstract

Aim
Trialkyl phosphites attack 6-(aryliminomethyl)furobenzopyran-5-ones regiospecifically at the carbon–carbon double bond of the γ-pyrone ring to yield new 1,2-addition phosphonate products for which structures have been respectively assigned.
Methods
The alkyl phosphites attacked the monoanils at the azomethine carbon of the C=N bond to yield corresponding phosphonate adducts when reactions were carried out in the presence of a controlled amount of acetic acid. Phosphonates could also be obtained by the reaction of dialkyl phosphites with anils . Structures of the new phosphonates were elucidated by elemental analyses as well as spectroscopic methods. The H and C nuclear magnetic resonance and infrared measurements were helpful tools in confirming the structures of the new products.
Results and conclusion
The insecticidal activities of phosphonates and their respective regioisomers against adult (Glover), which infest cotton crops, were determined. The structure–activity relationship has been discussed.

Keywords