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Phosphorus, Sulfur, and Silicon and the Related Elements Volume 185, 2010 - Issue 12
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Original Articles

Synthesis of the Phosphonoanalogue of Benzo[c]pyroglutamic Acid

Georgiy O. Kachkovskyi Institute of Bioorganic Chemistry and Petrochemistry of the National Academy of Sciences of Ukraine, Kyiv, Ukraine
&
Oleg I. Kolodiazhnyi Institute of Bioorganic Chemistry and Petrochemistry of the National Academy of Sciences of Ukraine, Kyiv, Ukraine
Pages 2441-2448 | Received 28 Dec 2009, Accepted 07 Feb 2010, Published online: 19 Nov 2010
 
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Abstract

Phosphonic analogue 1 of benzo[c]pyroglutamic acid was synthesized by three-step synthesis starting from N-tert-butylphtalimide and triethylphosphite. The acid-catalyzed, oxidative cascade conversion of phosphonate 11 to phthalimide and phosphoric acid diethyl ester was observed. A mechanism for this transformation was proposed.

Acknowledgments

This work was supported by the STCU, grant No. 3558.

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