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Allenylphosphine oxides as simple scaffolds for phosphinoylindoles and phosphinoylisocoumarins.


ABSTRACT: A range of phosphinoylindoles was prepared in one-pot from functionalized propargyl alcohols and a suitable P(III) precursor via a base-mediated reaction. The reaction proceeds via the intermediacy of allenylphosphine oxides. Similarly, phosphinoylisocoumarins were prepared from allenylphosphine oxides in a trifluoroacetic acid-mediated reaction; the latter also acts as a solvent. Interestingly, in the presence of wet trifluoroacetic acid, in addition to phosphinoylisocoumarins, phosphorus-free isocoumarins were also obtained. Key products were characterized by single crystal X-ray crystallography.

SUBMITTER: Gangadhararao G 

PROVIDER: S-EPMC4077435 | biostudies-literature | 2014

REPOSITORIES: biostudies-literature

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Allenylphosphine oxides as simple scaffolds for phosphinoylindoles and phosphinoylisocoumarins.

Gangadhararao G G   Kotikalapudi Ramesh R   Nagarjuna Reddy M M   Swamy K C Kumara KC  

Beilstein journal of organic chemistry 20140502


A range of phosphinoylindoles was prepared in one-pot from functionalized propargyl alcohols and a suitable P(III) precursor via a base-mediated reaction. The reaction proceeds via the intermediacy of allenylphosphine oxides. Similarly, phosphinoylisocoumarins were prepared from allenylphosphine oxides in a trifluoroacetic acid-mediated reaction; the latter also acts as a solvent. Interestingly, in the presence of wet trifluoroacetic acid, in addition to phosphinoylisocoumarins, phosphorus-free  ...[more]

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