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Paper | Regular issue | Vol 43, No. 9, 1996, pp.1893-1900
Published online, 1st January, 1970
DOI: 10.3987/COM-96-7477
Convenient Access to 3,4,5-Trisubstituted Pyridines

Angela De Munno,* Vincenzo Bertini, Nevio Picci, Francesca Iemma, and Marco Pocci

*Dipartimento di Chimica e Chimica Industriale, Universita di Pisa, Via Risorgnimento 35, I-56126 Pisa, Italy

Abstract

The reaction of 3,5-dochloro-4-pyridinecarbonitrile towards nucleophilic substitution of chlorine atoms and nucleophilic addition to the cyano group has been studied in presence of different nucleophiles and solvents in order to evidence the best conditions for the synthesis of 3,4,5-trifunctionalized pyridines. Besides the products of substitution of only one chlorine atom, 3,5-bis(ethylthio)-4-pyridinecarbonitrile and 3,5-bis(tert-butylthio)-4-pyridinecarbonitrile have been prepared in high yields and the reduction of their cyano to amino group has been studied in order to obtain model molecules and new selective inhibitors of extramitochondrial amine oxidase enzymes.