A serendipitous conversion of enaminolactone nitriles with primary amines: a new synthesis of substituted 2-aminopyridine derivatives

Fluorescent probes based on acridine derivatives and their application in dynamic monitoring of cell polarity variation

“…Firstly, compounds 3, 5 or 6 were obtained by the reaction of malononitrile with isophorone, 3-hydro-3-methyl-2-butanone or 2-aminobenzenethiol, and compound 4 was obtained by the reaction of 3-hydroxy-3-methyl-2-butanone and ethyl 2-cyanoacetate using the existing methods. [25][26][27][28] Secondly, the acridine ring of the classical dye matrix was introduced into the probe structure, and probes 1a-d (yields: 26.9% (1a), 51.6% (1b), 17.8% (1c), and 84.8% (1d)) were synthesized by the reaction between 9-acridine carboxaldehyde and the cyano compounds 3-6. Their structures were characterized using IR, 1 H NMR, and 13 C NMR spectroscopy and HRMS analyses as shown in the ESI.…”

Catalyzed reaction of enaminonitrile with primary amines by SbF3: synthesis of new 2-aminosubstituted-pyridine-fused δ-lactones

“…In the absence of acid, the reaction proceeded very slowly and the yield obtained was very poor (<10%) contrary to the results obtained with γ-lactones. 18 Thus, we have tested protic and Lewis catalysts. As protic acids, pentafluoroanilinium triflate (PFAT) was found the more efficient among ß-alanine, APTS, oxalic, camphosulfonic and sulfamic acids.…”

“…Recently, we focused on the preparation of bioactive nitrogen-containing heterocycles and we have shown that the synthesis of 2-aminopyridines from enaminolactone nitriles and primary aliphatic and aromatic amines was promising and constituted a valuable strategy. 18 Thus, we have reported a new method for the synthesis of 2-aminopyridines fused with a five-membered lactone (γ-lactone). A novel synthesis of 3-cyano-2aminopyridine derivatives then, from enaminonitrile and various primary amines have been also studied.…”

Efficient multicomponent synthesis of 2-aminopyridines catalysed by basic mesoporous materials

“…In the continuation of our research program on the development of green methodologies in the synthesis of biological important compounds using readily available, inexpensive and environmentally friendly catalysts [28][29][30][31][32][33][34], we wish to report in this work a new multicomponent reaction of 2-aminopyridines using mesoporous catalysts.…”