Microwave mediated synthesis of spiro-(indoline-isoxazolidines): mechanistic study and biological activity evaluation

R. Raunak, Vineet Kumar, Shubhasish Mukherjee, P. Poonam, Ashok K. Prasad, Carl E. Olsen, Susan Jeanne Cline Schäffer, Sunil K. Sharma, Arthur C. Watterson, William Errington, Virinder S. Parmar

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

Regioisomeric spiro-(indoline-isoxazolidines) have been synthesized in moderate yields by the cycloaddition reaction between ethyl (3-indolylidene)acetate and various substituted α,N-diphenylnitrones, using environmentally benign microwave technology. A novel concerted reaction mechanism is described that explains the preferential formation of the regioisomeric spiro-(indoline-isoxazolidine) analog 6 over 5. These compounds were screened for anti-mycobacterial and anti-invasive activities against tumor cells.
Original languageEnglish
JournalTetrahedron
Volume61
Issue number23
Pages (from-to)5687-5697
ISSN0040-4020
DOIs
Publication statusPublished - 2005

Cite this

Raunak, R., Kumar, V., Mukherjee, S., Poonam, P., Prasad, A. K., Olsen, C. E., Schäffer, S. J. C., Sharma, S. K., Watterson, A. C., Errington, W., & Parmar, V. S. (2005). Microwave mediated synthesis of spiro-(indoline-isoxazolidines): mechanistic study and biological activity evaluation. Tetrahedron, 61(23), 5687-5697. https://doi.org/10.1016/j.tet.2005.03.027