CuI-catalyzed hetarylation of natural di- and polyamines with halopyridines
- Authors: Panchenko S.P.1, Averin A.D.1, Lyakhovich M.S.1, Abel A.S.1, Maloshitskaya O.A.1, Beletskaya I.P.1
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Affiliations:
- Department of Chemistry, M. V. Lomonosov Moscow State University
- Issue: Vol 66, No 9 (2017)
- Pages: 1611-1617
- Section: Full Articles
- URL: https://journals.rcsi.science/1066-5285/article/view/241231
- DOI: https://doi.org/10.1007/s11172-017-1932-3
- ID: 241231
Cite item
Abstract
Copper(i)-catalyzed hetarylation of natural diamines (putrescine, cadaverine, and hexane-1,6-diamine), their analogs (propane-1,3-diamine and decane-1,10-diamine), as well as natural tri- (spermidine) and tetraamines (spermine) with 2-bromo, 2-iodo-, and 3-iodopyridines was studied. The CuI—2-isobutyrylcyclohexanone (10—20 mol.%) catalytic system provides the best results in the synthesis of target N,N´-dipyridinyl diamine derivatives. In some cases, an increase in the catalyst loading leads to an increase in the yields of the dihetarylated compounds. In the case of tri- and tetraamines, this catalytic system favors the predominant hetarylation of the primary amino groups with 2-bromopyridine and 3-iodopyridine.
About the authors
S. P. Panchenko
Department of Chemistry, M. V. Lomonosov Moscow State University
Email: averin@org.chem.msu.ru
Russian Federation, 3 Build., 1 Leninskie Gory, Moscow, 119991
A. D. Averin
Department of Chemistry, M. V. Lomonosov Moscow State University
Author for correspondence.
Email: averin@org.chem.msu.ru
Russian Federation, 3 Build., 1 Leninskie Gory, Moscow, 119991
M. S. Lyakhovich
Department of Chemistry, M. V. Lomonosov Moscow State University
Email: averin@org.chem.msu.ru
Russian Federation, 3 Build., 1 Leninskie Gory, Moscow, 119991
A. S. Abel
Department of Chemistry, M. V. Lomonosov Moscow State University
Email: averin@org.chem.msu.ru
Russian Federation, 3 Build., 1 Leninskie Gory, Moscow, 119991
O. A. Maloshitskaya
Department of Chemistry, M. V. Lomonosov Moscow State University
Email: averin@org.chem.msu.ru
Russian Federation, 3 Build., 1 Leninskie Gory, Moscow, 119991
I. P. Beletskaya
Department of Chemistry, M. V. Lomonosov Moscow State University
Email: averin@org.chem.msu.ru
Russian Federation, 3 Build., 1 Leninskie Gory, Moscow, 119991