Premium
Formal [4+2] Cycloaddition of o ‐ Aza ‐Quinone Methide for the Synthesis of 1,4‐Heterocycle‐Fused Quinolines
Author(s) -
Gharpure Santosh J.,
Nanda Santosh K.,
Fartade Dipak J.
Publication year - 2021
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202100074
Subject(s) - chemistry , quinone methide , intramolecular force , cycloaddition , quinoline , tandem , sulfoxide , stereochemistry , quinone , functional group , pummerer rearrangement , combinatorial chemistry , medicinal chemistry , organic chemistry , catalysis , acetic anhydride , materials science , polymer , composite material
Abstract A protocol involving intramolecular formal [4+2]‐cycloaddition of in situ generated o‐aza ‐quinone methide for the facile synthesis of 1,4‐heterocycle‐fused quinoline motifs is demonstrated. The cascade involved tandem C−O, C−C, and C−N bond formation and also exhibited excellent functional group tolerance. Enantiomerically enriched 1,4‐oxazepino quinolines were synthesized using alkynols derived from L‐amino acids. The sulfoxide embedded quinolines were transformed to pentacyclic 1,4‐thiepino tethered indeno‐quinoline scaffolds via Pummerer cyclization.