88775-49-9Relevant academic research and scientific papers
Photochemistry of 2-(3,4,5-Trimethoxyphenyl)-4-(3,4-methylenedioxyphenyl)-4-oxo-2-butenonitrile (β-Cyanochalchone) and Its Related Compounds
Ishikawa, Tsutomu,Koseki, Nobuyuki,Furukawa, Tomoko,Sakurada, Eri (Kawanabe),Koseki, Chiharu,et al.
, p. 9287 - 9302 (2007/10/02)
Photochemistry of the titled compounds both iin solid state and in solution is described.The (Z)-isomers of β-substituted chalchones (5,8 and 9) mainly dimerized into topochemically favored single cyclobutane dimers (10,14 and 13) in solid state photoreac
Studies on the chemical constituents of rutaceous plants. L. Development of a versatile method for the synthesis of antitumor-active benzo[c]phenanthridine alkaloids. (2). Preparation of 2-aryl-1-tetralone derivatives
Ishii,Kawanabe,Harada,et al.
, p. 3039 - 3055 (2007/10/02)
The synthetic pathway from 2,4-bisaryl-4-oxobutyramide (3) to 2-aryl-1-tetralone (4), which is the key intermediate in the Robinson synthesis of antitumor-active benzo[c]phenanthridine alkaloids was improved. Treatment of the model keto-amide (3a) under the reported basic conditions gave γ-keto-α,β-unsaturated acid (9) and degradation products. Reduction of the 2,4-bisaryl-4-oxobutyramide (3) with sodium borohydride gave 2,4-bisaryl-4-hydroxybutyramide (16) which could easily be hydrogenolyzed to give 2,4-bisarylbutyramide (15). However, this transformation also tended to give a γ-lactam derivative (17), unfortunately. We succeeded in the direct hydrogenolysis of the 2,4-bisaryl-4-oxobutyramide (3) to the 2,4-bisarylbutyramide (15), which could be hydrolyzed to the corresponding acid (5) without difficulty. The direct hydrolysis of the 2,4-bisaryl-4-oxobutyronitrile (2) to the 2,4-bisaryl-4-oxobutyric acid (6) as reported by Cheng et al. was also examined. Ten 2-aryl-1-tetralones (4) required as starting materials for syntheses of various benzo[c]phenanthridine alkaloids were prepared.
