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Synthesis 2010(17): 2990-2996  
DOI: 10.1055/s-0030-1258158
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

1-Propanephosphonic Acid Cyclic Anhydride (T3P) as an Efficient Promoter for the Lossen Rearrangement: Application to the Synthesis of Urea and Carbamate Derivatives

Basavalingappa Vasantha, Hosahalli P. Hemantha, Vommina V. Sureshbabu*
Peptide Research Laboratory, Department of Studies in Chemistry, Central College Campus, Dr. B. R. Ambedkar Veedhi, Bangalore University, Bangalore 560 001, India
e-Mail: hariccb@hotmail.com; e-Mail: sureshbabuvommina@rediffmail.com; e-Mail: hariccb@gmail.com;
Further Information

Publication History

Received 30 March 2010
Publication Date:
07 July 2010 (online)

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Abstract

The synthesis of hydroxamic acids starting from carboxylic acids employing 1-propanephosphonic acid cyclic anhydride (T3P) activation is described. Application of ultrasonication accelerates this conversion. Further, the T3P has also been employed to activate the hydroxamates, leading to isocyanates via the Lossen rearrangement. The isocyanates were trapped with suitable nucleophiles to afford the corresponding ureas and carbamates.

Key words

T3P - hydroxamic acids - Lossen rearrangement - isocyanates

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