98770-80-0Relevant academic research and scientific papers
Synthesis and 1,3-Dipolar Cycloaddition Reaction of Homoadamantane-Incorporated Nitrones and Rearrangement of the Cycloadducts to Homoadamantane-Fused Pyrroles
Yu, Yang,Ohno, Masatomi,Eguchi, Shoji
, p. 823 - 832 (2007/10/02)
The bridging nitrones 7, 8 incorporated in a homoadamantane ring system were obtained by oxidation of 4-azahomoadamantane 5, 6 with SeO2/H2O2.The 1,3-dipolar cycloaddition reaction of these nitrones with the electron-deficient alkynes proceeded regiospeci
SYNTHESIS OF 4-AZAHOMOADAMANT-4-ENE N-OXIDES AND THEIR 1,3-DIPOLAR CYCLOADDITION REACTIVITY
Yu, Yang,Ohno, Masatomi,Eguchi, Shoji
, p. 4965 - 4968 (2007/10/02)
Nitrones incorporated in a homoadamantane ring system, which were obtained by SeO2-H2O2 oxidation of 4-azahomoadamantane, underwent 1,3-dipolar cycloaddition reaction with electron-deficient alkynes (not with alkenes) to give 4-substituted isoxazoline spe
Synthesis of 4-Azahomoadamantanopyrroles and Related Derivatives by Enamine Cyclizations and 1,3-Dipolar Cycloadditions
Eguchi, Shoji,Wakata, Yuichi,Sasaki, Tadashi
, p. 1729 - 1745 (2007/10/02)
Treatment of 5-methyl- (1a) and 5-ethyl-4-azahomoadamant-4-ene (1b) with α-haloketones (2a-d) in the presence of triethylamine afforded 4-azahomoadamantanopyrrole derivatives (5a-f) in 14-77percent yields.Reaction of 4-azahomoadamant-4-ene (1c) with tetracyanoethylene oxide generated the corresponding dicyanomethylide (8) which was trapped with dimethyl acetylenedicarboxylate (DMAD) and methyl propiolate (MP) to afford the corresponding 4-azahomoadamantanopyrroles (10) and (11a), respecively, after aromatization.A non-stabilized methylide (13) was also successfully generated from the corresponding trimethylsilyl iminium iodide (12) by desilylation and trapped with DMAD and MP to afford the corresponding Δ3-pyrroline (14), pyrroles (15), (17a) and (17b).
