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1 article(s) from Kotikalapudi, Ramesh

Allenylphosphine oxides as simple scaffolds for phosphinoylindoles and phosphinoylisocoumarins

G. Gangadhararao,
Ramesh Kotikalapudi,
M. Nagarjuna Reddy and
K. C. Kumara Swamy

Beilstein J. Org. Chem. 2014, 10, 996–1005, doi:10.3762/bjoc.10.99

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Graphical Abstract

Scheme 1: Reaction of P(III)-Cl precursors with propargyl alcohols leading to phosphorus based (a) N-hydroxyi...

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Figure 1: Functionalized propargyl alcohols 1a–m and 2a–j used in the present study.

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Scheme 2: Synthesis of functionalized allenes 3a–c, 3m and 4a–j.

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Scheme 3: Reaction of functionalized allenes 3a and 3m leading to phosphinoylindoles. Conditions: (i) K₃PO₄ (...

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Figure 2: Molecular structure of compound 7. Hydrogen atoms (except PCH) are omitted for clarity. Selected bo...

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Figure 3: Molecular structure of compound 9. Hydrogen atoms (except NH) are omitted for clarity. Selected bon...

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Scheme 4: Synthesis of phosphinoylindole from allene 3a in a single step.

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Scheme 5: One-pot preparation of substituted phosphinoylindoles 6 and 9–19 from functionalized alcohols.

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Scheme 6: Possible pathway for the formation of phosphinoyl indoles 6 and 9–19.

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Scheme 7: Synthesis of phosphinoylisocoumarins from functionalized allenes.

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Figure 4: Molecular structure of 20. Selected bond lengths [Å] with estimated standard deviations are given i...

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Scheme 8: Possible pathway for the formation of phosphinoylisocoumarins.

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Scheme 9: Reaction of allenes in wet trifluoroacetic acid.

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Figure 5: Molecular structure of 33. Selected bond lengths [Å] with estimated standard deviations are given i...

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Scheme 10: Possible pathway for the formation of isocoumarins 30–35 (along with 21–23 and 27–29).

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Published 02 May 2014

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