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Blue LED Mediated Intramolecular C-H Functionalization and Cyclopropanation of Tryptamines: Synthesis of Azepino[4, 5-b]indoles and Natural Product Inspired Polycyclic Indoles
Chauhan J., Ravva M.K., Gremaud L.,
Published in American Chemical Society
PMID: 32453580
Volume: 22
Issue: 11
Pages: 4537 - 4541
We report a novel blue LED mediated intramolecular C-H functionalization of tryptamine derivatives to generate azepino[4, 5-b]indoles (4) in moderate to good yields. By altering the substitution at the tryptamine nitrogen, intramolecular cyclopropanation is achieved in high yields under the same reactions condition to provide natural product inspired polycyclic indoles (6), which are further transformed to spiropiperidino (5 and 8) indoles in decent yields. The mechanism of formation of the compounds was investigated through DFT studies. © 2020 American Chemical Society.
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Published in American Chemical Society
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