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Beilstein J. Org. Chem. 2014, 10, 996–1005, doi:10.3762/bjoc.10.99
Graphical Abstract
Scheme 1: Reaction of P(III)-Cl precursors with propargyl alcohols leading to phosphorus based (a) N-hydroxyi...
Figure 1: Functionalized propargyl alcohols 1a–m and 2a–j used in the present study.
Scheme 2: Synthesis of functionalized allenes 3a–c, 3m and 4a–j.
Scheme 3: Reaction of functionalized allenes 3a and 3m leading to phosphinoylindoles. Conditions: (i) K3PO4 (...
Figure 2: Molecular structure of compound 7. Hydrogen atoms (except PCH) are omitted for clarity. Selected bo...
Figure 3: Molecular structure of compound 9. Hydrogen atoms (except NH) are omitted for clarity. Selected bon...
Scheme 4: Synthesis of phosphinoylindole from allene 3a in a single step.
Scheme 5: One-pot preparation of substituted phosphinoylindoles 6 and 9–19 from functionalized alcohols.
Scheme 6: Possible pathway for the formation of phosphinoyl indoles 6 and 9–19.
Scheme 7: Synthesis of phosphinoylisocoumarins from functionalized allenes.
Figure 4: Molecular structure of 20. Selected bond lengths [Å] with estimated standard deviations are given i...
Scheme 8: Possible pathway for the formation of phosphinoylisocoumarins.
Scheme 9: Reaction of allenes in wet trifluoroacetic acid.
Figure 5: Molecular structure of 33. Selected bond lengths [Å] with estimated standard deviations are given i...
Scheme 10: Possible pathway for the formation of isocoumarins 30–35 (along with 21–23 and 27–29).