Access to densely functionalized spirocyclopentenonyl oxindole frameworks via aza- and carbo-Piancatelli rearrangement. Issue 26 (22nd June 2022)

• Record Type: Journal Article
• Authors: Pramanik, Sourav; Jagadeesh, Chenna; Chatterjee, Ayan; Debnath, Subhas Chandra; Saha, Jaideep
• Is Part Of: Organic & biomolecular chemistry. Volume 20:Issue 26(2022)
• Page Start: 5249
• Page End: 5253
• Publication Date: 2022-06-22
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d2ob00883a
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : The Piancatelli rearrangement on an oxindole-based template enables access to highly functionalized spirooxindole moieties. Abstract : A new strategy for access to spirocyclopentenonyl oxindole frameworks is disclosed. Suitably anchored furfuryl alcohol at C3 of an oxindole was used for the aza-Piancatelli rearrangement, which furnished spirocyclic aminocyclopentenone frameworks with catalytic phosphomolybdic acid. The scope of the transformation was extended to the carbo-Piancatelli rearrangement with various indole derivatives.