32294-64-7Relevant academic research and scientific papers
Mitsunobu Reaction Using Basic Amines as Pronucleophiles
Huang, Hai,Kang, Jun Yong
, p. 6604 - 6614 (2017)
A novel protocol for extending the scope of the Mitsunobu reaction to include amine nucleophiles to form C-N bonds through the utilization of N-heterocyclic phosphine-butane (NHP-butane) has been developed. Both aliphatic alcohols and benzyl alcohols are suitable substrates for C-N bond construction. Various acidic nucleophiles such as benzoic acids, phenols, thiophenol, and secondary sulfonamide also provide the desired products of esters, ethers, thioether, and tertiary sulfonamide with 43-93% yields. Importantly, C-N bond-containing pharmaceuticals, Piribedil and Cinnarizine, have been synthesized in one step from the commercial amines under this Mitsunobu reaction system.
Synthesis and transformations of phosphorus imidazolidines (1,3-diaza-2-phospholidines)
Das,Zuckerman
, p. 1028 - 1030 (2007/10/08)
Four new derivatives of the phosphorus imidazolidine ring system have been prepared by animation of dichlorophosphines with variously N,N′-disubstituted ethylenediamines. The nmr spectra of the N-CH3 substituted rings show a sharp doublet for these protons and a multiplet for the methylene bridge protons, while the N-phenyl derivatives show a sharp doublet for the methylene bridge protons at 60 and 100 MHz contrary to expectations on the basis of the pyramidal stereochemistry of phosphorus(III). These observations are interpreted in terms of the stereochemistry and dynamics of the diazaphos-pholidine heterocycles. The phosphorus imidazolidines are transformed to their boron analogs in an exothermic reaction with phenylboron dichloride with the release of dichlorophosphine, but the reaction is not reversible. Treatment of the phosphorus ring with arsenic trichloride yields a solid whose mass spectrum shows a peak at the highest mass corresponding to the ten-membered ring dimer of the known arsenic imidazolidine.
