5278-38-6Relevant academic research and scientific papers
Ruthenium-catalyzed cyclization of anilides with substituted propiolates or acrylates: An efficient route to 2-quinolinones
Manikandan, Rajendran,Jeganmohan, Masilamani
supporting information, p. 3568 - 3571 (2014/07/21)
A Ru-catalyzed cyclization of anilides with propiolates or acrylates affording 2-quinolinones having diverse functional groups in good to excellent yields is described. Later, 2-quinolinones were converted into 3-halo-2-quinolinones and 2-chloroquinolines
Synthesis of substituted coumarins and 2-quinolinones by cycloisomerisation of (hydroxy/aminophenyl)propargyl alcohols
Sridhar Reddy, Maddi,Thirupathi, Nuligonda,Babu, Madala Hari
, p. 5803 - 5809 (2012/11/07)
A new cycloisomerization strategy for the synthesis of coumarins and quinolinones is described. The addition of ethoxyacetylide to 2-hydroxyacetophenones directly resulted in 4-substituted coumarins by 6-endo-dig cycloisomerisation of the intermediate 3-ethoxy-1-(2-hydroxyphenyl)- 2-propyn-1-ols. Under similar conditions, 2-aminoacetophenone produced 2-ethoxyquinoline, a masked quinolinone, which was converted into the quinolinone by acid treatment. N-Protected intermediate 8 was isolated and converted into the quinolinone [with In(OTf)3 or H2SO 4] or the 3-iodo-2-quinolinone (with I2 and H +).
Facile synthesis of 3-substituted and 1,3-disubstituted quinolin-2(1H)-ones from 2-nitrobenzaldehydes
Park, Kwanghee Koh,Jung, Jin Young
, p. 2095 - 2105 (2007/10/03)
2-Nitrobenzaldehydes were reduced with iron powder to 2-aminobenzaldehydes, which were reacted immediately with acyl chlorides to provide 2-carboxamidobenzaldehydes (1) with overall yields of 71-90 %. Reaction of 1 with base provided 3-substituted quinolin-2(1H)-ones with 63-97 % yields. Treatment of 1 with methyl iodide and base gave 1-methyl-3-substituted quinolin-2(1H)-ones with 82-95 % yields, whereas the treatment with isopropyl iodide gave 1-isopropyl-3-substituted quinolin-2(1H)-ones with 7-42 % yields.
