期刊
TETRAHEDRON
卷 65, 期 26, 页码 5062-5073出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2009.02.062
关键词
Halogenation; Cross-coupling; Imidazo[1,5-a]pyridine; Fluorescence
资金
- Ministry of Education, Culture, Sports, Science and Technology of Japan [19020020]
- Grants-in-Aid for Scientific Research [19020020] Funding Source: KAKEN
The halogenation of 3-arylimidazo[1,5-a]pyridines was carried out with iodine, bromine, N-chlorosuccinimide, and 1-fluoro-2,4,6-trimethylpyridinium tetrafluoroborate as halogenating agents to give selectively halogenated products 1-halo-3-arylimidazo[1,5-a]pyridines in good to excellent yields. Kumada-Tamao-Corriu cross-coupling of the obtained 1-iodo-3-arylimidazo[1,5-a]pyridines and aryl Grignard reagents led to 1,3-diarylated imidazo[1,5-a]pyridines in good to excellent yields. Suzuki-Miyaura cross-coupling of the 1-bromo-3-phenylimidazo[1,5-a]pyridine and p- or m-methoxycarbonylphenylboronic acids furnished the coupling product in respective yields of 91% and 61%. The obtained 1,3-diarylated imidazo[1,5-a]pyridines showed a wide variety of fluorescent emissions in a wavelength range of 449-533 nm with improved quantum yields compared to monoarylated ones. (C) 2009 Elsevier Ltd. All rights reserved.
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