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,beta-dinitrostyrene (3a) with Na(2)S(2)O(4)/Zn(II) at pH 4. The latter procedure was successfully extended to the conversion of the 2,beta-dinitrostyrenes 3b and 3c to 5,6-dibenzyloxyindole (4b) and 5,6-diacetoxyindole (4c) in good-to-high yields

Expedient synthesis of 5,6-dihydroxyindole and derivatives via an improved Zn(II)-assisted 2,b-dinitrostyrene approach / Novellino, Luisa; D'Ischia, Marco; Prota, G. I. U. S. E. P. P. E.. - In: SYNTHESIS. - ISSN 0039-7881. - STAMPA. - 5:(1999), pp. 793-796. [10.1055/s-1999-3469]

Expedient synthesis of 5,6-dihydroxyindole and derivatives via an improved Zn(II)-assisted 2,b-dinitrostyrene approach.

D'ISCHIA, MARCO;
1999

Abstract

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,beta-dinitrostyrene (3a) with Na(2)S(2)O(4)/Zn(II) at pH 4. The latter procedure was successfully extended to the conversion of the 2,beta-dinitrostyrenes 3b and 3c to 5,6-dibenzyloxyindole (4b) and 5,6-diacetoxyindole (4c) in good-to-high yields
1999
Expedient synthesis of 5,6-dihydroxyindole and derivatives via an improved Zn(II)-assisted 2,b-dinitrostyrene approach / Novellino, Luisa; D'Ischia, Marco; Prota, G. I. U. S. E. P. P. E.. - In: SYNTHESIS. - ISSN 0039-7881. - STAMPA. - 5:(1999), pp. 793-796. [10.1055/s-1999-3469]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11588/142206
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