Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 6, Pages 2835-2842Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b02455
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Funding
- National Natural Science Foundation of China and Jiangsu Province [21202058, BK20161307]
- Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD)
- Foundation of Jiangsu Normal University [15XLA06]
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An efficient synthesis of diversified indolizine derivatives was developed via CuBr-catalyzed reaction of pyridines, methyl ketones and alkenoic acids under solvent free conditions in oxygen atmosphere. This synthesis involves cascade processes of copper-catalyzed bromination of the methyl ketone, 1,3-dipolar cycloaddition of the pyridinium ylide with the alkenoic acid, followed by oxidative decarboxylation and dehydrogenative aromatization of the primary cycloadduct. By this protocol, a wide range of indoliznes with different substitution patterns were selectively prepared in one pot from simple substrates in good to excellent yields.
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