A core switching strategy to pyrrolo[2, 3-b]quinolines and diazocino[1, 2-a]indolinones. Issue 38 (6th September 2016)

• Record Type: Journal Article
• Authors: Jones, Alan M.; Patterson, Stephen; Lorion, Magali M.; Slawin, Alexandra M. Z.; Westwood, Nicholas J.
• Is Part Of: Organic & biomolecular chemistry. Volume 14:Issue 38(2016)
• Page Start: 8998
• Page End: 9011
• Publication Date: 2016-09-06
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c6ob01566b
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Two novel core-switching rearrangements to natural product-like privileged scaffolds that proceed in up to 99% yield have been developed. Abstract : Two novel core-switching rearrangements to natural product-like privileged scaffolds that proceed in up to 99% yield have been developed. The deviation away from planarity of the central N -acyl urea carbonyl, caused by the structure of the medium-sized ring, dictates the exclusive reaction outcome. Proposed mechanisms and products for the reaction pathways are supported by small molecule X-ray crystallography and an isolated intermediate. Twenty-four novel rearrangement products are reported.