jo4003773_si_002.cif (52.75 kB)

Rearrangement of 4‑Amino-3-halo-pyridines by Nucleophilic Aromatic Substitution

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posted on 07.06.2013, 00:00 by Matthäus Getlik, Brian J. Wilson, M. Monzur Morshed, Iain D. G. Watson, Doris Tang, Pandiaraju Subramanian, Rima Al-awar
The reaction of 3-halo-4-aminopyridines with acyl chlorides and triethylamine is described. The pyridin-4-yl α-substituted acetamide products were obtained in moderate to high yields. The presented rearrangement reaction, in which the presumed N-acylated intermediate reacts intramolecularly via nucleophilic aromatic substitution, results in a formal two-carbon insertion.