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Effective syntheses of quinoline-7,8-diol, 5-amino- l-DOPA, and 3-(7,8-dihydroxyquinolin-5-yl)- l-alanine
Journal article   Peer reviewed

Effective syntheses of quinoline-7,8-diol, 5-amino- l-DOPA, and 3-(7,8-dihydroxyquinolin-5-yl)- l-alanine

Markus R Heinrich and Wolfgang Steglich
Tetrahedron, Vol.59(46), pp.9231-9237
10/11/2003
DOI: https://doi.org/10.1016/j.tet.2003.02.004

Abstract

3-aminocatechols Baeyer–Villiger reaction l-DOPA derivatives quinolines
A modification of the Baeyer–Villiger reaction allows the conversion of aromatic 2-hydroxy-3-nitroketones and aldehydes into 3-nitrocatechols, which can be reduced to 3-aminocatechols. Reaction of the latter with acrolein yields quinoline-7,8-diols under exceptionally mild conditions. This new reaction sequence was successfully applied to the synthesis of the title compounds. Graphic

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