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tert ‐Butoxide‐Mediated Synthesis of 3,4′‐Biquinolines from 2‐Aminochalcones
Author(s) -
Jeon Jiye,
Lee So Young,
Cheon CheolHong
Publication year - 2019
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.201900029
Subject(s) - chemistry , aromatization , conjugate , nucleophile , michael reaction , stoichiometry , nucleophilic addition , medicinal chemistry , molecule , sodium , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , mathematical analysis , mathematics
A novel protocol to synthesize 3,4’‐biquinolines from 2‐aminochalcones in the presence of a stoichiometric amount of sodium tert ‐butoxide as the nucleophilic promotor was developed. Conjugate addition of tert ‐butoxide to 2‐aminochalcones provided the corresponding enolates, which underwent Michael addition to another molecule of 2‐aminochalcone to afford a dimeric species of 2‐aminochalcones. Subsequent cyclization between the amino and carbonyl groups followed by aromatization provides 3,4’‐biquinoline products. Various 2‐aminochalcones were submitted to this protocol and the desired 3,4’‐biquinoline products were obtained in good to high yields in a short reaction time.