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An Expeditious and Metal‐Free Synthetic Route towards Quinolones, Naphthyridones and Benzonaphthyridones
Author(s) -
Victor Napoleon John,
Muraleedharan Kannoth Manheri
Publication year - 2014
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.201300891
Subject(s) - chemistry , combinatorial chemistry , tandem , adduct , quinolone , derivative (finance) , stereochemistry , primary (astronomy) , organic chemistry , antibiotics , biochemistry , materials science , physics , astronomy , financial economics , economics , composite material
An efficient, two‐step synthetic strategy has been developed to access the quinolone, naphthyridone and benzonaphthyridone classes of chemotherapeutic agents from Baylis–Hillman adducts. The method involves tandem aza‐Michael addition, S N Ar cyclisation followed by oxidation of the resulting 4‐hydroxy‐1,2,3,4‐tetrahydroquinoline or 4‐hydroxy‐1,2,3,4‐tetrahydro‐1,8‐naphthyridine derivative using IBX, and works well with substrates having a wide variety of substitution pattern.