The reactions between anilines and DMSO/HCl produce Tröger's bases in moderate yield. The Tröger's bases bearing an electron-withdrawing group can also be synthesized through this procedure. In this reaction, DMSO/HCl acts as formaldehyde equivalent.
Various nitromethylene derivatives were synthesized regioselectively. Compounds 8a-f were obtained by the reaction of 1-((5-chloropyridin-2-yl)methyl)-2-(nitromethylene)-octahydro-1H-cyclopenta[d]-pyrimidine (3) with primary amines and formaldehyde. The synthesized compounds were identified by 1H NMR, HRMS (EI), and IR, and preliminary bioassays indicated that most of them showed moderate insecticidal activities against Aphis craccivora. The relationship between hydrophobicity and biological activity was also discussed.
The N-monoalkylation of 2-or 3-aminopyridines by a carboxylic acid and sodium borohydride afforded the corresponding alkylaminopyridine under mild conditions in good yields. N-Alkylaminopyridines are important intermediate for preparing N-containing heterocycles, such as "flytrap" aminopyridinium-based anion hosts and pharmaceuticals.
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