Abstract
A domino approach to bridged cycloocta[b]indolone through a cascade of aza-Piancatelli rearrangement/Friedel-Crafts alkylation is developed. This transformation has been realized by reaction of an indole-tethered 2-furylcarbinol and substituted aniline in the presence of a Lewis acid to initiate aza-Piancatelli rearrangement followed by an in situ intramolecular Friedel-Crafts alkylation to access bridged tetracyclic frameworks in one pot.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 8555-8560 |
| Number of pages | 6 |
| Journal | Organic Letters |
| Volume | 22 |
| Issue number | 21 |
| DOIs | |
| State | Published - Nov 6 2020 |
| Externally published | Yes |
Bibliographical note
Funding Information:The authors thank the Council of Scientific and Industrial Research (CSIR), Ministry of Science and Technology, Government of India for research facilities. N. R. thanks Cipla Ltd. and AcSIR for doctoral studies. P. R. S. thanks the CSIR for research fellowship. K. N. thanks the CSIR-Indian Institute of Chemical Technology (IICT) for fellowship and research facilities under the National Laboratories Scheme of CSIR (No.11/3/Rectt.-2020). S. C. thanks the Science and Engineering Research Board (SERB), Government of India for J C Bose fellowship (SB/S2/JCB-002/2015). We gratefully acknowledge Dr Balasubramanian Sridhar, Laboratory of X-ray Crystallography, CSIR-IICT, for X-ray analysis.
Publisher Copyright:
© 2020 American Chemical Society.