A core switching strategy to pyrrolo[2,3-b]quinolines and diazocino[1,2-a]indolinones.
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.
School of Chemistry and Biomedical Sciences Research Complex, University of St Andrews, North Haugh, St Andrews, Fife, Scotland KY16 9ST, UK. a.m.jones@mmu.ac.uk njw3@st-andrews.ac.uk.
Alan M
AM
Jones
Stephen
S
Patterson
Magali M
MM
Lorion
Alexandra M Z
AM
Slawin
Nicholas J
NJ
Westwood