• Cyclodiphosphazanes as synthetic probes: P-C/P-N bond formation from the reaction with functionalized propargyl alcohols and 𝑁-hydroxy substrates

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      https://www.ias.ac.in/article/fulltext/jcsc/127/02/0197-0207

    • Keywords

       

      Cyclodiphosphazanes; cistrans isomerism; allenes; indoles; rearrangement; propargyl alcohols; phosphano-heterocycles.

    • Abstract

       

      Phosphano-indoles were synthesized in a fairly straightforward route from the reaction of simple cyclodiphosphazanes [XP(𝜇-N-t-Bu)2PY] [X=Y=NH-$t$-Bu (1a); X=Y=NH-i-Pr (1b)] with o-aminophenyl functionalized propargyl alcohols. The reaction occurs via an allene intermediate formed by PIII-O-C$\to$PV(O)-C rearrangement, followed by cyclization utilizing the central allenic carbon and the –NH2 functionality. In a similar way, cyclodiphosphazanes [XP(𝜇-N-t-Bu)2PY] [X=Y=Cl (1c); X=Cl, Y=NH-t-Bu(1d)] have been treated with N-hydroxy substrates to obtain novel PIII-O-N$\to$PV(O)-N rearranged products.X-ray structures of the four products, 2-(1-phenyl-ethyl)-3-[(t-Bu)NH)P(𝜇-N-t-Bu)2P(O)]-indole [14], cis-{[-C(=O)-C6H4-C(=O)-]-N-P(=O)-N-t-Bu}2[cis-18], trans-{[-C(=O)-C6H4-C(=O)-]-N-P(=O)-N-t-Bu}2 [trans-18] and cis-[(t-BuNH)P(𝜇-N-t−Bu)2P(=O)-N{-C(=O)-CH2-CH2-C(=O)-}] [cis-19] are also reported

    • Author Affiliations

       

      G Gangadhararao1 K C Kumara Swamy1

      1. School of Chemistry, University of Hyderabad, Hyderabad 500 046, India
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