Title: Access to 2-aminopyridines : compounds of great biological and chemical significance
Authors : Bolliger, Jeanne L.
Oberholzer, Miriam
Frech, Christian M.
Published in : Advanced synthesis & catalysis
Volume(Issue) : 353
Issue : 6
Pages : 945
Pages to: 954
Publisher / Ed. Institution : Wiley
Issue Date: 2011
License (according to publishing contract) : Licence according to publishing contract
Type of review: Peer review (Publication)
Language : English
Subject (DDC) : 540: Chemistry
Abstract: 2‐Aminopyridines are key structural cores of bioactive natural products, medicinally important compounds, and organic materials and thus, extremely valuable synthetic targets. The few reported 6‐substituted 2‐aminopyridines and the lack of flexible, efficient and general applicable methods for their synthesis demonstrates the urgent need of new methods for their preparation. Reactions between 2,6‐dibromopyridine and primary or secondary, cyclic or acyclic, and aliphatic or aromatic amines were shown to selectively yield the respective 6‐bromopyridine‐2‐amines in very high yields which were successfully used as substrates for subsequent C-C cross‐coupling reactions. The recently introduced dichloro‐bis[1‐(dicyclohexylphosphanyl)piperidine]palladium (1) was used as catalyst for the cross‐coupling of 6‐bromopyridine‐2‐amines with arylboronic acids, diaryl‐ and dialkylzinc reagents or olefins and hence, is also an excellent C-C cross‐coupling catalyst for this type of substrate. Moreover, all the reaction protocols presented were in each of the catalyses uniformly applied. The scope of both the amination and the cross‐coupling reactions are well defined and allow one to simply adapt the reaction protocols directly to other amines and/or coupling partners and, thus, provide for the first time a very flexible and generally applicable reaction protocol to get access to 2‐aminopyridines.
Departement: Life Sciences and Facility Management
Publication type: Article in scientific Journal
DOI : 10.1002/adsc.201000942
ISSN: 1615-4150
1615-4169
URI: https://digitalcollection.zhaw.ch/handle/11475/10466
Appears in Collections:Publikationen Life Sciences und Facility Management

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