Condensation of enynones readily available from cheap starting material with pyrazolamines provides easy access to fluorescent 7-(trimethylsilylethynyl)pyrazolo[1,5-a]pyrimidines. The reaction is straightforward, does not require the use of any additional reagents or catalysts, and can be performed without inert atmosphere. Various substituents and functional groups in both enynone and pyrazolamine are tolerated. The presented method features full regioselectivity, high isolated yields, and simplicity of both setup and product purification. Fluorescent properties of the obtained pyrazolopyrimidines were studied.
The oxidative addition of N-aminophthalimide to substituted2-vinylfurans provides monophthaloylhydrazones of (2Z)-hexa-2,5-diene-1,4-dione derivativesi nstead of 2-furylaziridines by proceeding through an aziridination of the endocyclic furan C=Cb ond followed by ar egio-and stereoselective rearrangement of the bicyclic intermediate. The formation of stable aziridines can then occur through the aziridination of the (E)-C=Cb ondo ft hese phthaloylhydrazones. Detailed structure elucidations and mechanistic considerations are provided.
2,3‐Diaryl‐1‐phthalimidoaziridines and 2,3‐diaryl‐1‐phthalimidoaziridine‐2‐carbonitriles are found to readily undergo thermal rearrangement into imines via 1,2‐migration of the phthalimido group and accompanying C—C bond cleavage.
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