The reactions of β‐azolylenamines 1 with sulfonyl azides 2 in acetonitrile furnished 1H‐4‐(azol‐5‐yl)‐1,2,3‐triazoles 3 in yields of 52–93 %. β‐Benzoylenaminones and β‐nitroenamine of type 1 also reacted with tosyl azide to form the same type of products 3, proving the generality and efficiency of the method for the synthesis of N‐unsubstituted 1,2,3‐triazoles. On the other hand, the reactions of 3‐(1‐aryl‐1,2,3‐triazol‐5‐yl)enamines with tosyl azide in the absence of a solvent afforded a mixture of (E)‐1‐dimethylamino‐2‐tosylaminoethenes 5 and N,N‐dimethyl‐N′‐tosylformamidine 6 in yields of 40–50 and 20 %, respectively. The formation of a variety of compounds from the reactions of enamines 1 with sulfonyl azides 2 is rationalized by the various possible transformations of the intermediate 5‐dimethylamino‐1,2,3‐triazolines 7.
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.
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