143925-57-9Relevant articles and documents
Exploratory Studies of α-Silylamino and α-Silylamido 2,5-Cyclohexadien-1-one SET Photochemistry. Methodology for Synthesis of Functionalized Hydroisoquinolines
Jung, Young Shik,Swartz, William H.,Xu, Wei,Mariano, Patrick S.,Green, Neal J.,Schultz, Arthur G.
, p. 6037 - 6047 (2007/10/02)
The electron-transfer (SET) photochemistry of selected α-silylamino and α-silylamido 2,5-cyclohexadienones has been explored with the intent of developing a novel and potentially efficient method for functionalized hydroisoquinoline synthesis.These substances, prepared by Birch reduction-alkylation-oxidation sequences, were found to undergo 9,10-dicyanoanthracene-SET-sensitized radical cyclization to form hydroisoquinolines in a highly regio- and stereoselective fashion and in modest to good yields.In contrast, the major direct irradiation reaction pathway followed by the α-silylamido-substituted systems involves type A rearrangement to bicyclic cyclohexenones or phenols.Direct irradiation of the α-silylamino analogs, on the other hand, brings about near-exclusive conversion to the corresponding hydroisoquinolines.The synthetic and mechanistic features of this study are described.
