Synthesis of tetracyclic benzoxazolo-indol-3-ones from isatogens and arynes through a [3+2]-cycloaddition and skeletal reorganization
| Title | Synthesis of tetracyclic benzoxazolo-indol-3-ones from isatogens and arynes through a [3+2]-cycloaddition and skeletal reorganization |
| Publication Type | Journal Article |
| Year of Publication | 2024 |
| Authors | Halnor, SV, Singh, M, Dhote, PS, Ramana, CV |
| Journal | Journal of Organic Chemistry |
| Volume | 89 |
| Issue | 20 |
| Pagination | 14919-14928 |
| Date Published | OCT |
| Type of Article | Article |
| ISSN | 0022-3263 |
| Abstract | 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. |
| DOI | 10.1021/acs.joc.4c01667 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 3.6 |
Divison category:
Organic Chemistry
Database:
Web of Science (WoS)