Synthesis of Tetracyclic Benzoxazolo-indol-3-ones from Isatogens and Arynes through a [3 + 2]-Cycloaddition and Skeletal Reorganization
The construction of an unprecedented tetracyclic benzoxazolo-indol-3-one scaffold has been executed through the [3 + 2]-cycloaddition of isatogens with arynes. The initially formed benzisoxazolo-indol-3-one intermediate undergoes a skeletal reorganization through a 1,3-sigmatropic shift/retro-Mannich reaction with the net formation of one C-N and two C-O bonds. The Lewis acid-catalyzed allylation of some of the resulting benzoxazolo-indol-3-ones resulted in oxazepino-indolones with promising photophysical properties.
Authors
- Swapnil V. Halnor (ORCID: https://orcid.org/0000-0001-5796-5856)
- Chepuri V. Ramana (ORCID: https://orcid.org/0000-0001-5801-311X)
- Pawan S. Dhote (ORCID: https://orcid.org/0000-0002-1073-6236)
- Maneesha Singh
Institutions
- National Chemical Laboratory (IN)
- Academy of Scientific and Innovative Research (IN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2024-10-08
- DOI
- https://doi.org/10.1021/acs.joc.4c01667
- Citations
- 4
- Primary Topic
- Cyclization and Aryne Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 1.00
Funders
- Department of Science and Technology, Ministry of Science and Technology, India
- Council of Scientific and Industrial Research, India
- Science and Engineering Research Board