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Paper | Regular issue | Vol 55, No. 11, 2001, pp.2075-2084
Published online, 1st January, 1970
DOI: 10.3987/COM-01-9303
3,5-Dichloro-4-pyridinecarbonitrile: A Multisite Substrate for Carbon Nucleophiles

Nevio Picci, Marco Pocci,* Annarosa Gugliuzza, Francesco Puoci, Angela De Munno, Francesca Iemma, and Vincenzo Bertini

*Dipartimento di Chimica e Tecnologie Farmaceutiche ed Alimentari, Università di Genova, Via Brigata Salerno, I-16147 Genova, Italy


The reactivity of 3,5-dichloro-4-pyridinecarbonitrile (1) towards lithium or magnesium organo-metallic reagent is described. Conditions for substitution of cyano with alkyl or phenyl group, alkylation at the position 2 with removal of the 5-positioned chlorine, and formation of methyl or phenyl dichloro-pyridyl imines are reported. The obtained 4-alkyl-3,5-dichloropyridines can undergo a further alkylation at the position 2. The 3,5-dichloro-4-pyridyl residue is shown to be a good leaving group in form of anion yielding 3,5-dichloropyridine either from 1 or 3,5-dichloro-4-pyridinecarboxaldehyde.