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Synthesis and Chemical Reactivity of the Novel 4‐Hydroxy‐6‐methyl‐2,5‐dioxo‐5,6‐dihydro‐2 H ‐pyrano[3,2‐ c ]quinoline‐3‐carboxaldehyde
Author(s) -
Ibrahim Magdy A.,
Hassanin Hany M.,
Gabr Yassin,
Alnamer Youssef A.
Publication year - 2018
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.3353
Subject(s) - chemistry , quinoline , formylation , reactivity (psychology) , reagent , nucleophile , medicinal chemistry , organic chemistry , stereochemistry , catalysis , medicine , alternative medicine , pathology
Vilsmeier–Haack formylation of 3‐(4‐hydroxy‐1‐methy1‐2‐oxo‐(1 H )‐quinolin‐3‐yl)‐3‐oxopropanoic acid ( 2 ) produced the novel 4‐hydroxy‐6‐methyl‐2,5‐dioxo‐5,6‐dihydro‐2 H ‐pyrano[3,2‐ c ]quinoline‐3‐carboxaldehyde ( 4 ). The chemical reactivity of carboxaldehyde 4 with a diversity of nitrogen nucleophilic reagents was studied, and a variety of products were obtained. Some 1,3,4‐oxadiazolyl/1,3,4‐thiadiazolyl/benzothiazolyl linked pyrano[3,2‐ c ]quinoline‐2,5(6 H )‐dione were efficiently synthesized. Structures of the new synthesized products were deduced on the basis of their analytical and spectral data.