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

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 nucleophi...

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Bibliographic Details
Published in:Organic letters 2016-03, Vol.18 (5), p.984-987
Main Authors: van der Heijden, Gydo, Jong, J. A. W. (Sjaak), Ruijter, Eelco, Orru, Romano V. A
Format: Article
Language:English
Subjects:
Amides
Analgesics, Opioid - chemical synthesis
Analgesics, Opioid - chemistry
Analgesics, Opioid - pharmacology
Combinatorial Chemistry Techniques
Cyanides - chemical synthesis
Cyanides - chemistry
Drug Discovery
Fentanyl - analogs & derivatives
Fentanyl - chemical synthesis
Fentanyl - chemistry
Fentanyl - pharmacology
Molecular Structure
Nitriles - chemical synthesis
Nitriles - chemistry
Pyridines - chemical synthesis
Pyridines - chemistry
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b00091