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Divergent Synthesis of 6- or 7-Aza-Indazoles via Intramolecular Diels-Alder Cascade of Pyrazines. | LitMetric

AI Article Synopsis

  • Pyrazines are highly reactive compounds that can participate in Diels-Alder reactions with certain activated partners, even at room temperature in a specific kind of reaction.
  • The study demonstrated a unique intramolecular cascade reaction leading to the formation of 6- or 7-aza-indazoles.
  • Researchers found that different substituents on the reaction precursor affected the distribution of the final products, and NMR studies were used to understand this selectivity better.

Article Abstract

Pyrazines are reactive 4π partners in intermolecular Diels-Alder cycloaddition with exceptionally activated dienophiles or in an intermolecular version at elevated temperatures. Herein, it is shown that an intramolecular cascade could occur even at room temperature, delivering a collection of 6- or 7-aza-indazoles. An interesting substituent effect of the cycloaddition precursor on the product distribution was uncovered, and NMR studies were conducted to gain insights into this unexpected selectivity.

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Source
http://dx.doi.org/10.1021/acs.orglett.3c03052DOI Listing

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