Tetrahedron

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

MR Heinrich, W Steglich

Index: Heinrich, Markus R.; Steglich, Wolfgang Tetrahedron, 2003 , vol. 59, # 46 p. 9231 - 9237

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Citation Number: 12

Abstract

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.