Nickel-Catalyzed [2+2+2] Cycloaddition of Diynes and Cyanamides.European J Org Chem. 2011 Jul; 2011(20-21):3815-3824.EJ
Abstract
A variety of bicyclic N,N-disubstituted 2-aminopyridines have been prepared from diynes and cyanamides by nickel-catalyzed [2+2+2] cycloaddition reactions. The reactions proceeded at room temperature with low catalyst loading to afford 2-aminopyridines in good to excellent yields. The method is amenable to both internal and terminal diynes and proceeds in a regioselective manner. A number of cyanamides with diverse functional group tolerance were used. The intermolecular version employing 3-hexyne and N-cyanopyrrolidine also afforded the desired N,N-disubstituted 2-aminopyridine in good yield.
Links
Pub Type(s)
Journal Article
Language
eng
PubMed ID
25346615
Citation
Stolley, Ryan M., et al. "Nickel-Catalyzed [2+2+2] Cycloaddition of Diynes and Cyanamides." European Journal of Organic Chemistry, vol. 2011, no. 20-21, 2011, pp. 3815-3824.
Stolley RM, Maczka MT, Louie J. Nickel-Catalyzed [2+2+2] Cycloaddition of Diynes and Cyanamides. European J Org Chem. 2011;2011(20-21):3815-3824.
Stolley, R. M., Maczka, M. T., & Louie, J. (2011). Nickel-Catalyzed [2+2+2] Cycloaddition of Diynes and Cyanamides. European Journal of Organic Chemistry, 2011(20-21), 3815-3824.
Stolley RM, Maczka MT, Louie J. Nickel-Catalyzed [2+2+2] Cycloaddition of Diynes and Cyanamides. European J Org Chem. 2011;2011(20-21):3815-3824. PubMed PMID: 25346615.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR
T1 - Nickel-Catalyzed [2+2+2] Cycloaddition of Diynes and Cyanamides.
AU - Stolley,Ryan M,
AU - Maczka,Michael T,
AU - Louie,Janis,
PY - 2014/10/28/entrez
PY - 2011/7/1/pubmed
PY - 2011/7/1/medline
KW - Alkynes
KW - Carbenes
KW - Cyanamides
KW - Cycloaddition
KW - Nickel
SP - 3815
EP - 3824
JF - European journal of organic chemistry
JO - European J Org Chem
VL - 2011
IS - 20-21
N2 - A variety of bicyclic N,N-disubstituted 2-aminopyridines have been prepared from diynes and cyanamides by nickel-catalyzed [2+2+2] cycloaddition reactions. The reactions proceeded at room temperature with low catalyst loading to afford 2-aminopyridines in good to excellent yields. The method is amenable to both internal and terminal diynes and proceeds in a regioselective manner. A number of cyanamides with diverse functional group tolerance were used. The intermolecular version employing 3-hexyne and N-cyanopyrrolidine also afforded the desired N,N-disubstituted 2-aminopyridine in good yield.
SN - 1434-193X
UR - https://www.unboundmedicine.com/medline/citation/25346615/Nickel_Catalyzed_[2+2+2]_Cycloaddition_of_Diynes_and_Cyanamides_
DB - PRIME
DP - Unbound Medicine
ER -
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