1251735-85-9Relevant articles and documents
Synthesis of chiral benzoacridinone derivatives by three-component condensation of [(1S,4Sr)-1,7,7-Trimethyl-bicyclo[2.2.1]hept-2-ylidene] acetaldehyde with naphthalen-1-amine and cyclic β-diketones
Koval'skaya,Kozlov,Dikusar
, p. 1121 - 1134 (2010)
Three-component condensation of [(1S,4S)-1,7,7-trimethylbicyclo[2.2.1]hept- 2-ylidene]acetalde-hyde with naphthalen-1-amine and cyclic β-diketones gave 7-[(1S,4S)-1,7,7-trimethylbicyclo[2.2.1]hept-2-ylidenemethyl]-7,8,9,10,11,12- hexahydro-7/f-benzo[c]acridin-8-one derivatives possessing three or more asymmetric carbon atoms. Steric factors were found to be responsible for the predominant formation of the (7R)-isomers (R/S 7:5) and orientation of substituents in the cyclohexenone fragment. The same factors determined complete regioselectivity of the reaction with methyl 2,4-dioxocyclohexane-1- carboxylates as dicarbonyl component, which led to exclusive formation of methyl 8-oxobenzoacridine-11-carboxylates. In the reaction of [(1S,4S)-1,7,7- trimethylbicyclo[2.2.1]hept-2-ylidene]acetaldehyde with naphthalen-1-amine and barbituric acid as dicarbonyl component, the only product was that formed by two-component condensation of barbituric acid with bicyclic aldehyde. Pleiades Publishing, Ltd., 2010.
