The 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.
The reaction of Sovol technical mixture of polychlorobiphenyls with sodium methoxide in bipolar aprotic solvents was studied. The reactivity of polychlorobiphenyls was evaluated using gas chromatography and gas chromatography3mass spectrometry.
a b s t r a c t
5-Bromopyrimidine reacts with 2,20 -bithiophene, [2,2 0 :5 0 ,2 00 ]terthiophene and 2-phenylthiophene in the presence of a palladium catalyst to give 5-(het)aryl substituted pyrimidines due to the palladiumcatalyzed arylearyl CeC coupling. However 5-bromo-4-(het)aryl-pyrimidines have been prepared from the same starting materials through the S N H -reaction catalyzed by a Lewis acid. Conditions for both types of reactions were optimized. All components of the reaction mixtures, including by-products, have been elucidated by gaseliquid chromatography/mass-spectrometry. Evidence for the structure of 4-and 5-bithiophenyl-substituted pyrimidines has first been obtained by means of X-ray crystallography analysis. Molecular orbital calculations (TDDFT), as well as the redox and optical measurements for all new compounds have also been performed.
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