Marta Feroci, Isabella Chiarotto, Gianpiero Forte, Giovanna Simonetti, Felicia Diodata D'Auria, Louis Maes, Daniela De Vita, Luigi Scipione, Laura Friggeri, Roberto Di Santo, Silvano Tortorella
The use of electrogenerated acetonitrile anion allows the alkylation of N-Boc-4-aminopyridine in very high yields, under mild conditions and without by-products. The high reactivity of this base is due to its large tetraethylammonium counterion, which leaves the acetonitrile anion "naked." The deprotection of the obtained compounds led to high yields in N-alkylated 4-aminopyridines. Nonsymmetrically dialkylated 4-aminopyridines were obtained by subsequent reaction of monoalkylated ones with t-BuOK and alkyl halides, while symmetrically dialkylated 4-aminopyridines were obtained by direct reaction of 4-aminopyridine with an excess of t-BuOK and alkyl halides...
2014: ISRN Organic Chemistry