Access to 2-aminopyridines : compounds of great biological and chemical significance

Bolliger, Jeanne L.; Oberholzer, Miriam; Frech, Christian M.

doi:10.1002/adsc.201000942

Publication type:	Article in scientific journal
Type of review:	Peer review (publication)
Title:	Access to 2-aminopyridines : compounds of great biological and chemical significance
Authors:	Bolliger, Jeanne L. Oberholzer, Miriam Frech, Christian M.
DOI:	10.1002/adsc.201000942
Published in:	Advanced Synthesis & Catalysis
Volume(Issue):	353
Issue:	6
Page(s):	945
Pages to:	954
Issue Date:	2011
Publisher / Ed. Institution:	Wiley
ISSN:	1615-4150 1615-4169
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 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.
URI:	https://digitalcollection.zhaw.ch/handle/11475/10466
Fulltext version:	Published version
License (according to publishing contract):	Licence according to publishing contract
Departement:	Life Sciences and Facility Management
Appears in collections:	Publikationen Life Sciences und Facility Management

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Bolliger, J. L., Oberholzer, M., & Frech, C. M. (2011). Access to 2-aminopyridines : compounds of great biological and chemical significance. Advanced Synthesis & Catalysis, 353(6), 945–954. https://doi.org/10.1002/adsc.201000942

Bolliger, J.L., Oberholzer, M. and Frech, C.M. (2011) ‘Access to 2-aminopyridines : compounds of great biological and chemical significance’, Advanced Synthesis & Catalysis, 353(6), pp. 945–954. Available at: https://doi.org/10.1002/adsc.201000942.

J. L. Bolliger, M. Oberholzer, and C. M. Frech, “Access to 2-aminopyridines : compounds of great biological and chemical significance,” Advanced Synthesis & Catalysis, vol. 353, no. 6, pp. 945–954, 2011, doi: 10.1002/adsc.201000942.

BOLLIGER, Jeanne L., Miriam OBERHOLZER und Christian M. FRECH, 2011. Access to 2-aminopyridines : compounds of great biological and chemical significance. Advanced Synthesis & Catalysis. 2011. Bd. 353, Nr. 6, S. 945–954. DOI 10.1002/adsc.201000942

Bolliger, Jeanne L., Miriam Oberholzer, and Christian M. Frech. 2011. “Access to 2-Aminopyridines : Compounds of Great Biological and Chemical Significance.” Advanced Synthesis & Catalysis 353 (6): 945–54. https://doi.org/10.1002/adsc.201000942.

Bolliger, Jeanne L., et al. “Access to 2-Aminopyridines : Compounds of Great Biological and Chemical Significance.” Advanced Synthesis & Catalysis, vol. 353, no. 6, 2011, pp. 945–54, https://doi.org/10.1002/adsc.201000942.