title: 2-Bromo-6-isocyanopyridine as a Universal Convertible Isocyanide for Multicomponent Chemistry.
abstract: The development of 2-isocyanopyridines as novel convertible isocyanides for multicomponent chemistry is reported. Comparison of 12 representatives of this class revealed 2-bromo-6-isocyanopyridine as the optimal reagent in terms of stability and synthetic efficiency. It combines sufficient nucleophilicity with good leaving group capacity of the resulting amide moiety under both basic and acidic conditions. To demonstrate the practical utility of this reagent, an efficient two-step synthesis of the potent opioid carfentanil is presented.
authors: Department of Chemistry and Pharmaceutical Sciences, Amsterdam Institute for Molecules, Medicines & Systems (AIMMS), VU University Amsterdam , De Boelelaan 1083, NL-1081 HV Amsterdam, The Netherlands.
authors: Gydo
authors: G
authors: van der Heijden
authors: Department of Chemistry and Pharmaceutical Sciences, Amsterdam Institute for Molecules, Medicines & Systems (AIMMS), VU University Amsterdam , De Boelelaan 1083, NL-1081 HV Amsterdam, The Netherlands.
authors: J A W Sjaak
authors: JA
authors: Jong
authors: Department of Chemistry and Pharmaceutical Sciences, Amsterdam Institute for Molecules, Medicines & Systems (AIMMS), VU University Amsterdam , De Boelelaan 1083, NL-1081 HV Amsterdam, The Netherlands.
authors: Eelco
authors: E
authors: Ruijter
authors: Department of Chemistry and Pharmaceutical Sciences, Amsterdam Institute for Molecules, Medicines & Systems (AIMMS), VU University Amsterdam , De Boelelaan 1083, NL-1081 HV Amsterdam, The Netherlands.
authors: Romano V A
authors: RV
authors: Orru
mesh_terms: D000577:Amides; D000701:Analgesics, Opioid / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D020650:Combinatorial Chemistry Techniques; D003486:Cyanides / Q000138:chemical synthesis* / Q000737:chemistry; D055808:Drug Discovery; D005283:Fentanyl / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D009570:Nitriles / Q000138:chemical synthesis / Q000737:chemistry*; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: C000609063:2-bromo-6-isocyanopyridine; D000577:Amides; D000701:Analgesics, Opioid; D003486:Cyanides; D009570:Nitriles; D011725:Pyridines; C017114:carfentanil; D005283:Fentanyl