Synthesis of strained pyridine-containing cyclyne via reductive aromatization.
The Sonogashira-Hagihara coupling reactions of 2,6-diiodopyridine and cis-3,6-diethynyl-3,6-dimethoxycyclohexa-1,4-diene or cis-9,10-diethynyl-9,10-dimethoxy-9,10-dihydroanthracene gave macrocyclic compounds having alternating 2,6-diethynylpyridine and 3,6-dimethoxycyclohexa-1,4-diene segments. Transformation of the C(3)-symmetric 2,6-diethynylpyridine-based cyclotrimer was efficiently achieved using tin-mediated reductive aromatization under mild conditions.
Miki
Koji
K
Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, 615-8510, Japan.
Fujita
Michiyasu
M
Inoue
Yuki
Y
Senda
Yoshinori
Y
Kowada
Toshiyuki
T
Ohe
Kouichi
K
D000480:Alkynes / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D047028:Macrocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011725:Pyridines / Q000737:chemistry*
D000480:Alkynes; D047028:Macrocyclic Compounds; D011725:Pyridines; C023666:pyridine