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14.4.1.1.1.2.2.2.9 Variation 9: Knoevenagel Condensation of 2-Hydroxybenzaldehydes with Malonic Acid and Its Derivatives

DOI: 10.1055/sos-SD-014-00294

Williams, A. C.; Camp, N.Science of Synthesis, (200314367.

Representative examples of this variation are shown in Scheme 19. 2-Hydroxybenzaldehydes react with {[(2-aminoethyl)amino]carbonyl}acetates and -thiocarbonyl}acetates to give 2-oxo-2H-1-benzopyran-3-carboxamides 57 (X=O) and -carbothioamides 57 (X=S), 2-hydroxybenzaldehydes react with malonic acid or diethyl malonate to give 2-oxo-2H-1-benzopyran-3-carboxylic acids 58 or -3-carboxylates 61, while reaction of 2-hydroxybenzaldehydes or 2-hydroxyphenyl ketones with malononitrile gives 2-oxo-2H-1-benzopyran-3-carbonitrile 59 and reaction with alkyl malonates gives 2-oxo-2H-1-benzopyran-3-carboxylates 60.

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References


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