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- Title
Sequential Hydroperoxylation and Amberlyst‐15 Catalyzed Hock‐type Rearrangement of Spiroepoxy/Spiroaziridine Oxindoles for the Synthesis of 2‐Hydroxybenzo[b][1,4]oxazin‐3(4H)‐ones.
- Authors
Saleh, S. K. Abu; Mondal, Ananda Shankar; Senapati, Swarup; Hajra, Saumen
- Abstract
A sequential one‐pot direct strategy for the synthesis of 2‐hydroxy‐2‐substituted‐2H‐benzo[b][1,4]oxazin‐3(4H)‐ones is developed under ambient conditions with moderate to good yields (up to 75 %) by regioselective ring‐opening of spiro‐epoxy/aziridine oxindoles with 50 % aq. H2O2 followed by rearrangement reaction in presence of amberlyst‐15 catalyst. Further, sequential reaction with aldehydes/ketones and carbonyldiimidazole (CDI) gave spiro[benzo[b][1,4]oxazine‐2,4′‐[1,3]dioxolan]‐3(4H)‐ones and spiro[benzo[b][1,4]oxazine‐2,4′‐[1,3]dioxolane]‐2′,3(4H)‐diones, respectively.
- Subjects
OXINDOLES; REARRANGEMENTS (Chemistry); KETONES; ALDEHYDES; AZIRIDINES
- Publication
Asian Journal of Organic Chemistry, 2024, Vol 13, Issue 2, p1
- ISSN
2193-5807
- Publication type
Article
- DOI
10.1002/ajoc.202300581