868765-19-9Relevant academic research and scientific papers
A new route to acridines: Pauson-Khand reaction on quinoline-bearing 1-En-7-ynes leading to novel tetrahydrocyclopenta[c]acridine-2,5-diones
Patin, Amaury,Belmont, Philippe
, p. 2400 - 2406 (2005)
Efficient Pauson-Khand reactions on quinolines bearing 1-en-7-ynes features gave tetrahydrocyclopenta[c]acridine derivatives. The quinoline intermediates were obtained in two steps: a Sonogashira reaction with functionalized alkynes (TMS, Bu, Ph, CHB
FeCl3·6H2O-catalyzed facile and efficient synthesis of pyrano[4,3-b]quinolines and isochromenes
Asthana, Mrityunjaya,Singh, Jay Bahadur,Singh, Radhey M.
, p. 615 - 618 (2016/01/20)
An inexpensive 1 mol % FeCl3·6H2O reagent has been developed for the synthesis of 1,3-disubstituted 1H-pyrano[4,3-b]quinolines from o-arylethnylquinonylmethanol via 6-endo-dig cyclization of alcoholic -OH onto alkynes in good to excellent yields. The reaction conditions were successfully exploited on primary and tertiary alcohol analogs. The reagent was further generalized with the aromatic alcohol analogs providing the synthesis of isochromenes in good yields. The enhancement in the reaction rates and yields from primary to secondary to tertiary alcohols could be attributed to inductive effect of alkyl groups which enhanced the nucleophilicity of hydroxyl group and accelerated the cyclization mode.
