112213-27-1Relevant academic research and scientific papers
Synthesis of 8,9,10,11,12,13,13a,14-Octahydro-7,11;9,13-dimethanoazoninoisoquinolin-5(7H)-ones and Some Related Derivatives by Photocyclization Reactions of 5-Methylene-4-aroyl- and -acryloyl-4-azatricyclo3,8>undecanes (4-Azahomoadamantanes)
Eguchi, Shoji,Asai, Koji,Takeuchi, Hisato,Sasaki, Tadashi
, p. 1171 - 1176 (2007/10/02)
5-Methylene-4-aroyl- and -acryloyl-4-azatricyclo3,8>undecanes (2a-h) have been prepared by acylation of 5-methyl-4-azatricyclo3,8>undec-4-ene (1).Irradiation of 4-aroyl derivatives (2a-d) afforded 2- or 4-substituted 8,9,10,11,12,13,13a,14-octahydro-7,11;9,13-dimethanoazoninoisoquinolin-5(7H)-ones (3a-d) in good yields via enamide photocyclization.DDQ oxidation of (3a-d) gave the corresponding hexahydroisoquinolin-5(7H)-ones (4a-d).Among the acryloyl derivatives, only the methacryloyl derivative (2g) afforded the enamide photocyclization product (5) in a lower yield, the other acryloyl derivatives (2e,f,h) when irradiated yielding the corresponding vinylogous amide derivatives (6a-c) via a 1,3-acyl shift.
