Synthesis and cyclisation studies of (E)-2-aryl-1-methyl-3-styrylquinolin-4(1H)-ones

The synthesis of (E)-2-aryl-1-methyl-3-styrylquinolin-4(1H)-ones, through the Heck reaction of 2-aryl-3-iodo-1-methyl-quinolin-4(1H)-ones with styrene is described. 2-Aryl-3-iodo-1-methyl-2-quinolin-4(1H)-ones can be obtained efficiently in a two-step transformation, methylation followed by in situ...

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Bibliographic Details
Published in:Tetrahedron 2015-10, Vol.71 (40), p.7717-7721
Main Authors: Rocha, Djenisa H.A., Pinto, Diana C.G.A., Silva, Artur M.S.
Format: Article
Language:English
Subjects:
(E)-2-Aryl-1-methyl-3-styrylquinolin-4(1H)-ones
4-Arylfuro[3,2-c]quinolones
Benzo[c]acridin-7(12H)-ones
Heck reaction
N-methylation
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Summary:The synthesis of (E)-2-aryl-1-methyl-3-styrylquinolin-4(1H)-ones, through the Heck reaction of 2-aryl-3-iodo-1-methyl-quinolin-4(1H)-ones with styrene is described. 2-Aryl-3-iodo-1-methyl-2-quinolin-4(1H)-ones can be obtained efficiently in a two-step transformation, methylation followed by in situ cyclization of N-(2-acetylphenyl)benzamides into 2-aryl-1-methylquinolin-4(1H)-ones, which underwent selective 3-iodination with iodine and a catalytic amount of Can. Cyclisation studies of (E)-2-aryl-1-methyl-3-styrylquinolin-4(1H)-ones under high temperature or photoinduced electrocyclisation lead to 4-aryl-2-phenylfuro[3,2-c]quinolines and 12-methyl-5-phenylbenzo[c]acridin-7(12H)-ones. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2015.07.058