Journal
CHEMCATCHEM
Volume 8, Issue 6, Pages 1046-1050Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cctc.201501261
Keywords
annulation; C-H activation; natural products; nitrogen heterocycles; ruthenium
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Funding
- Department of Science and Technology [SR/FT/CS-001/2010]
- Council of Scientific and Industrial Research, India [OLP1206]
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Pyrrole- and indole-fused isocoumarins constitute important structural units in natural products and pharmacophores, although the direct and selective bifunctionalization of pyrrole and indole remain a challenge. Herein, we report a one-pot synthesis of pyrrole- and indole-fused isocoumarins from simple 1-methylpyrrole-2-carboxylic acid and 1-methylindole-3-carboxylic acid by annulation with alkynes in the presence of a ruthenium(II) catalyst based on [RuCl2(p-cymene)](2) with Cu(OAc)(2)H2O as the oxidant in DMF. This ruthenium(II)-catalyzed transformation was shown to be profitably performed in water as the solvent. The reaction, which involves carboxylate coordination, activation of the heterocyclic sp(2) C-H bond, and insertion of the alkyne, is regioselective, which leads to good yields of the isocoumarins.
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