Synthesis of 2-arylamino-3-cyanoquinolines via a cascade reaction through a nitrilium intermediate

A new method for the preparation of 2-amino-3-cyanoquinolines from readily available aryldiazonium salts, 2-aminoarylketones, and malononitrile via a cascade reaction is reported. This one-pot approach involves the in situ generation of an N-arylnitrilium intermediate from the direct reaction of ary...

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Published inOrganic & biomolecular chemistry Vol. 18; no. 5; pp. 975 - 982
Main Authors Ramanathan, Mani, Wan, Jing, Liu, Yi-Hung, Peng, Shie-Ming, Liu, Shiuh-Tzung
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 07.02.2020
Royal Society of Chemistry
Subjects
Amination
Cascade chemical reactions
Chemistry
Chemistry, Organic
Crystallography
Malononitrile
NMR
Nuclear magnetic resonance
Organic compounds
Physical Sciences
Quinolines
Salts
Science & Technology
ARYLDIAZONIUM SALTS
QUINOLINE
FACILE SYNTHESIS
KINASE INHIBITOR
MECHANISM
ANNULATION
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Summary:A new method for the preparation of 2-amino-3-cyanoquinolines from readily available aryldiazonium salts, 2-aminoarylketones, and malononitrile via a cascade reaction is reported. This one-pot approach involves the in situ generation of an N-arylnitrilium intermediate from the direct reaction of aryldiazonium salts and malononitrile, which undergoes intermolecular amination, Knoevenagel condensation, and then aromatization to yield the desired compound in moderate to good yields. This methodology features a quick assembly of C2 and C3 functionalized quinolines.
Bibliography:ObjectType-Article-1
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ISSN:1477-0520
1477-0539
DOI:10.1039/c9ob02427a