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2-Bromo-6-isocyanopyridine as a Universal Convertible Isocyanide for Multicomponent Chemistry

Gydo van der Heijden, J. A. W. (Sjaak) Jong, Eelco Ruijter* and Romano V. A. Orru*

*Department of Chemistry and Pharmaceutical Sciences, VU University Amsterdam, De Boelelaan 1083, NL-1081 HV Amsterdam, The Netherlands, Email: e.ruijtervu.nl, r.v.a.orruvu.nl

G. van der Heiden, J. A. W. Jong, E. Ruijter, R. V. A. Orru, Org. Lett., 2016, 18, 984-987.

DOI: 10.1021/acs.orglett.6b00091 (free Supporting Information)


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Abstract

2-bromo-6-isocyanopyridine as novel convertible isocyanide for multicomponent chemistry combines sufficient nucleophilicity with good leaving group capacity of the resulting amide moiety under both basic and acidic conditions. An efficient two-step synthesis of the potent opioid carfentanil demonstrates the practical utility of this reagent.

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Key Words

Ugi Reaction, Hydrolysis


ID: J54-Y2016