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December 1, 1983The Journal of Organic Chemistry

Inverse electron demand Diels-Alder reactions of 4,6-dimethyl-2-oxo-2H-pyran-5-carboxylic acid esters and morpholino enamines: regiospecific preparation of 3- or 4-substituted-2,6-dimethylbenzoates

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Authors

HGHenry L. GingrichEmory UniversityDRD. M. ROUSHMerck & Co., Inc., Rahway, NJ, USA (United States)WSWilliam A. Van SaunMerck & Co., Inc., Rahway, NJ, USA (United States)

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Implication

Chemical synthesis study demonstrates regiospecific preparation of 3- or 4-substituted-2,6-dimethylbenzoates via pyrone-enamine cycloadditions, highlighting a targeted route for substituted aromatics.

Key Points

  • Investigate inverse electron demand Diels-Alder reactions of 4,6-dimethyl-2-oxo-2H-pyran-5-carboxylic acid esters with morpholino enamines for the regiospecific synthesis of substituted dimethylbenzoates.
  • Coupled 4,6-dimethyl-2-oxo-2H-pyran-5-carboxylic acid ester derivatives with morpholino enamines under inverse electron demand cycloaddition conditions.
  • Analyzed reaction regioselectivity to achieve targeted substitution patterns at the 3- or 4-positions of the resulting 2,6-dimethylbenzoate framework.
  • Achieved regiospecific synthesis of 3- or 4-substituted-2,6-dimethylbenzoate esters from pyrone and enamine starting materials.
  • Demonstrated predictable regiochemical control governed by enamine structure and pyrone ester substitution during the cycloaddition process.

Cite This Study

Gingrich et al. (1983) studied this question.

synapsesocial.com/papers/6aa9e60cb5e32d7ae6557c09https://doi.org/10.1021/jo00173a017
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