Azide-Mediated Detosylation
of N-Tosylpyrroloiminoquinones and N-Tosylindole-4,7-quinones

Swayamprabha P. Patel; Dwayaja H. Nadkarni; Srinivasan Murugesan; Jason R. King; Sadanandan E. Velu

doi:10.1055/s-0028-1083570

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Synlett 2008(18): 2864-2868
DOI: 10.1055/s-0028-1083570

LETTER

Azide-Mediated Detosylation of N-Tosylpyrroloiminoquinones and N-Tosylindole-4,7-quinones

Swayamprabha P. Patel, Dwayaja H. Nadkarni, Srinivasan Murugesan, Jason R. King, Sadanandan E. Velu*
Department of Chemistry, University of Alabama at Birmingham, 901 14th Street South, Birmingham, AL 35294, USA
Fax: +1(205)9342543; e-Mail: svelu@uab.edu;

Further Information

Publication History

Received 28 April 2008
Publication Date:
21 October 2008 (online)

Abstract
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Abstract

The utility of NaN₃ as a reagent for the detosylation of N-tosylpyrroloiminoquinones and N-tosylindole-4,7-quinones is described. The NaN₃-mediated detosylation is carried out in polar aprotic solvents such as DMF and DMSO. The reaction occurs under neutral, mild conditions and results in good to excellent yields of the detosylated quinones.

Key words

sodium azide - detosylation - quinones - indoloquinone - pyrroloiminoquinones.

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