Ring Expansion of Isatins via 1,2-Phospha-Brook Rearrangement: A Route to the Synthesis of 2-Quinolinone-Derived p-Quinone Methides.
J Org Chem
; 87(24): 16313-16327, 2022 12 16.
Article
in En
| MEDLINE
| ID: mdl-36459618
ABSTRACT
A Lewis acid-mediated one-carbon homologation approach to installing a 2-quinolinone core embedded with para-quinone methides, in a high yield of up to 92%, and with high regioselectivity has been developed. Also, post-synthetic modifications, including C-P, C-S, and C-C bond formations, have been demonstrated by the 1,6-addition of suitable nucleophiles. Further, cyclopropanation of 2-quinolinone-embedded p-QM is also demonstrated affording a contiguous quaternary spiro center.
Full text:
1
Database:
MEDLINE
Main subject:
Quinolones
/
Indolequinones
/
Isatin
Language:
En
Journal:
J Org Chem
Year:
2022
Type:
Article
Affiliation country:
India