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Synthesis 1999; 1999(5): 793-796
DOI: 10.1055/s-1999-3469
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Expedient Synthesis of 5,6-Dihydroxyindole and Derivatives via an Improved Zn(II)-Assisted 2,β-Dinitrostyrene Approach

Luisa Novellino* , Marco d'Ischia, Giuseppe Prota
  • *Department of Organic and Biological Chemistry, University of Naples "Federico II", Via Mezzocannone 16, I-80134 Naples, Italy; Fax +39(81)5 52 12 17; E-mail: prota@cds.unina.it
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Publication Date:
31 December 1999 (online)

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A facile 3-step synthesis of 5,6-dihydroxyindole (4a) is reported, featuring the Zn(II)-controlled regioselective nitration of 3,4-dihydroxynitrostyrene (2) with tetranitromethane at pH 8.0 and the reductive cyclization of the resulting 4,5-dihydroxy-2,β-dinitrostyrene (3a) with Na2S2O4/Zn(II) at pH 4. The latter procedure was successfully extended to the conversion of the 2,β-dinitrostyrenes 3b and 3c to 5,6-dibenzyloxyindole (4b) and 5,6-diacetoxyindole (4c) in good-to-high yields.

5,6-dihydroxyindoles - 2,β-dinitrostyrenes - regioselective nitration - tetranitromethane - Zn(II) ions - sodium dithionite