96151-20-1Relevant academic research and scientific papers
Synthesis of Some Novel Functionalized Monoazatricyclic Ring Systems via Intramolecular Cycloaddition of N-(Bicycloalkenyl)nitrones
Eguchi, Shoji,Furukawa, Yoshio,Suzuki, Takanori,Kondo, Kazumoto,Sasaki, Tadashi,et al.
, p. 1895 - 1899 (1985)
The intramolecular cycloaddition of C-phenyl-N-(endo-bicyclooct-6-en-3-ylmethyl)nitrone (3) geneerated in situ from the corresponding hydroxylamine and benzaldehyde gave the adduct 4 in a high yield.Reductive cleavage of 4 afforded 2-endo-hydroxy-4-endo-phenyl-5-azatricyclo3,9>undecane (6).The intramolecular cycloadditions of unsymmetrical N-(endo-bicyclohept-5-en-2-ylmethyl)nitrones (11a,b) and N-(endo-bicyclooct-5-en-2-ylmethyl)nitrones (23a,b) occurred regiospecifically to afford the adducts 12a, b and 24a,b, respectively.Reductive cleavage of these adducts provided a convenient route to functionalized 5-azatricyclo3,8>decanes (15a,b, 16, 17) and 5-azatricyclo3,8>undecanes (27a,b, 28, 29), respectively.The regiochemical and stereochemical assignments of 12a and 24a were proven by X-ray analysis of the methiodides 14a and 26a.
