Abstract
AbstractThe combination of the Suzuki–Miyaura cross‐coupling and nucleophilic aromatic substitution of hydrogen reactions is a versatile tool for the syntheses of 4‐(1R‐pyrrol‐2‐yl)‐ and 4‐(1R‐indol‐3‐yl)‐5‐(hetero)aryl‐substituted pyrimidines from commercially available 5‐bromopyrimidine. The SNH [AE, (addition–elimination)] and SNH [AO, (addition–oxidation)] reactions of 5‐bromopyrimidine with pyrroles and indoles were studied by gas chromatography–mass spectrometry. The structures of the intermediate σH adducts as well as the pyrrole‐(hetero)arylpyrimidine and indole‐(hetero)arylpyrimidine dyads were established for the first time by X‐ray crystal structure analysis.
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