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The Convenient Synthesis of 11‐Methyl‐3,8‐disubstituted‐12‐aryl‐3,4,7,8,9,12‐hexahydro‐1 H ‐chromeno[2,3‐ b ]quinoline‐1,10(2 H )‐dione Derivatives
Author(s) -
Han GuangFan,
Zhao LiJun,
Chen LiZhuang,
Du JiaWei,
Wang ZhongXia
Publication year - 2015
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.1930
Subject(s) - chemistry , knoevenagel condensation , quinoline , aryl , hydrolysis , catalysis , crystal structure , medicinal chemistry , ethylene glycol , malononitrile , elemental analysis , ethylene , condensation , condensation reaction , single crystal , organic chemistry , crystallography , alkyl , physics , thermodynamics
The 2‐arylidene‐3‐oxobutanenitrile derivatives 2 were prepared by the Knoevenagel condensation between aldehydes and 3‐oxobutanenitrile 1 , which was obtained by acid hydrolysis of β‐aminocrotononitrile. 3‐Acetyl‐2‐amino‐4 H ‐chromen‐5(6 H )‐one derivatives 3 were synthesized by reaction of 2‐arylidene‐3‐oxobutanenitrile 2 and 5‐substituted‐1,3‐cyclohexanedione in ethylene glycol . The 11‐methyl‐3,8‐disubstituted‐12‐aryl‐3,4,7,8,9,12‐hexahydro‐1 H ‐chromeno[2,3‐ b ]quinoline‐1,10(2 H )‐dione derivatives 4 were obtained by Friedländer reaction of compounds 3 with 5‐substituted‐1,3‐cyclohexanedione, using p ‐toluenesulfonic acid monohydrate as catalyst. The structures of all novel compounds were characterized by elemental analysis, IR, MS, and 1 H NMR spectra. The crystal and molecular structure of compound 4f has been determined by single crystal XRD analysis.