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An exceptionally mild synthetic strategy using cascade reaction for 3,4‐dihydronaphthyridinones having aliphatic substituent on amide nitrogen
Author(s) -
Tazawa Aoi,
Ishizawa Kohei,
Ando Junki,
Watanabe Masayuki,
Azumaya Isao,
Hikawa Hidemasa,
Tanaka Minoru
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201802104
Subject(s) - amide , chemistry , reductive amination , substituent , amination , cascade reaction , alkyl , ether , cascade , organic chemistry , combinatorial chemistry , reaction conditions , nitrogen , coupling reaction , catalysis , chromatography
Abstract A facile synthetic procedure for 3,4‐dihydronaphthyridinone derivatives is described. This synthetic route involves the cascade reaction of methyl nicotinate having an ethoxyvinyl group with various amines. The desired cyclization products were obtained using pyridylacetaldehyde formation and subsequent reductive amination/cyclization with amines. For the preparation of vinyl ether derivatives, we employed the coupling reaction, and the method would be applicable to various related substrates. Furthermore, all the reactions to N‐alkyl products proceeded rapidly at ambient temperature in good yields using simple and safe protocols. This strategy allows the generation of dihydronaphthyridinone derivatives containing various amines.