57103-58-9Relevant academic research and scientific papers
STUDIES ON THE CHEMICAL TRANSFORMATION OF ROTENOIDS. II. REACTIONS OF ROTENONE AND ROTENONONE WITH PRIMARY AMINES
Sakakibara, Jinsaku,Nagai, Shin-ichi,Akiyama, Teppei,Ueda, Taisei,Oda, Noriichi
, p. 1109 - 1117 (2007/10/02)
The ring transformations of rotenone and rotenonone by primary amines were investigated.The improved synthetic methods for rotenonone were also developed.Rotenone (1) underwent cleavage of C-12a and O-13 linkage to give alkylamines (2a-b), while rotenonone (5) gave 2-alkylcarbamoyl-4-alkylimino-8-methylethenyl-3-(2-hydroxy-4,5-dimethoxy)phenyl-8,9-dihydro-4H-furobenzopyrans (7a-d) as a result of nucleophilic attack on C-12 carbon.Compound 1 was oxidized bynitrosyl chloride or dimethyl sulfoxide in the presence of iodine and sulfuric acid to provide rotenonone (5) in improved yields respectively.
