Synthesis of Indolo[2,3/3,2-<i>c</i>]quinoline through Complementary PIDA/BF<sub>3</sub>·OEt<sub>2</sub> as Well as Pd(0)-Mediated Intramolecular Cyclization of Isomeric <i>N</i>-((Aryl)-<i>N</i>-(phenylsulfonyl)indolyl)methylbenzenesulfonamides
Herein, a straightforward facile synthesis of indolo[2,3-<i>c</i>]quinoline analogues was reported from 2-arylamino(phenylsulfonyl)methylindoles involving PIDA/BF<sub>3</sub>·OEt<sub>2</sub>-mediated intramolecular dehydrogenative coupling (IDC) as a key step. Even though isomeric 3-arylamino(phenylsulfonyl)methylindoles, upon interaction with PIDA/BF<sub>3</sub>·OEt<sub>2</sub>, led to complications, synthesis of the indolo[3,2-<i>c</i>]quinoline framework could be easily achieved from <i>N</i>-(2-iodoaryl)-<i>N</i>-indolylmethylbenzenesulfonamide by employing a Pd(0)-mediated intramolecular cyclization reaction. Under identical conditions, synthesis of indolo[2,3-<i>c</i>]quinolines was also accomplished from the respective <i>N</i>-(2-iodoaryl)-<i>N</i>-indolylmethylbenzenesulfonamides. The SRB assay of fluorine-bound indoloquinolines displayed nanomolar-level cytotoxicity against a nonsmall lung cancer cell line, NCI-H460.
Authors
- Vinayagam Pavunkumar
- Arasambattu K. Mohanakrishnan (ORCID: https://orcid.org/0000-0002-3758-4578)
- Kesavan Harikrishnan
Institutions
- University of Madras (IN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2024-08-09
- DOI
- https://doi.org/10.1021/acs.joc.4c01113
- Citations
- 3
- Primary Topic
- Chemical synthesis and alkaloids
- Type
- article
- Field-Weighted Citation Impact
- 0.75
Funders
- Department of Science and Technology, Ministry of Science and Technology, India
- Science and Engineering Research Board
- Rashtriya Uchchatar Shiksha Abhiyan