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, Jyoti (Department of Chemistry, School of Natural Sciences, Shiv Nadar University, Dadri, Chithera, Gautam Budh Nagar, Uttar Pradesh, India) ; Ravva, Mahesh K. (Department of Chemistry, SRM University AP, Neerukonda, Andhra Pradesh, India) ; Gremaud, Ludovic (School of Engineering and Architecture (HEIA-FR), HES-SO // University of Applied Sciences Western Switzerland) ; Sen, Subhabrata (Department of Chemistry, SRM University AP, Neerukonda, Andhra Pradesh, India)

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.


Article Type:
scientifique
Faculty:
Ingénierie et Architecture
School:
HEIA-FR
Institute:
ChemTech - Institut des technologies chimiques
Date:
2020-05
Pagination:
5 p.
Published in:
Organic Letters
Numeration (vol. no.):
2020, no. 22, pp. 4537-4541
DOI:
ISSN:
1523-7060
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 Record created 2020-09-01, last modified 2020-10-27

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