ChemInform Abstract: PREPARATION AND (1)H‐NMR SPECTRA OF SOME ADAMANTANE DERIVATIVES, 2‐FORMYLADAMANTANE, 2‐BROMO‐3‐METHYL‐2‐HOMOADAMANTENE, 4,4‐ADAMANTYLENE‐1,3‐DIOXANES AND SOME GEMINAL SUBSTITUTED ADAMANTANES, INCLUDING 2‐ADAMANTYLENECYCLOBUTANONE

Bernaert, E.; Danneels, Dirk; Anteunis, M.; Verhegge, G.

doi:10.1002/chin.197419237

Cited by 1 publication

(4 citation statements)

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“…The synthesis of this ketone was accomplished starting from 2-adamantanone 4 which was successively transformed to spiro [adamantane-2,2′-oxirane] 5 and aldehyde 6 (Farcasiu, 1972). In the past, this alcohol has been synthesized from the Grignard reaction between the epoxide 5 and methyl magnesium iodide (Bernaert et al, 1973) or between acetaldehyde and 2-adamantyl magnesium bromide (Yurchenko et al, 1987). In the past, this alcohol has been synthesized from the Grignard reaction between the epoxide 5 and methyl magnesium iodide (Bernaert et al, 1973) or between acetaldehyde and 2-adamantyl magnesium bromide (Yurchenko et al, 1987).…”

Section: Chemistrymentioning

confidence: 99%

“…Details for the preparation of 2-adamantanecarboxaldehyde 6 and 2-adamantyl methyl ketone 8 and cyclobutanone 22 are presented in the literature (Farcasiu, 1972;Bernaert et al, 1973;van Leusen & van Leusen, 1978). 2-Adamantanamine 3 was prepared by reductive amination of 2-adamantanone 4 (Borch et al, 1971).…”

Section: Chemistrymentioning

confidence: 99%

“…Due to its instability, this aldehyde was not isolated and was used promptly after its preparation for the synthesis of α−methyl-2-adamantanemethanol 7. In the past, this alcohol has been synthesized from the Grignard reaction between the epoxide 5 and methyl magnesium iodide (Bernaert et al, 1973) or between acetaldehyde and 2-adamantyl magnesium bromide (Yurchenko et al, 1987). Alcohol 7 was oxidized with Jones reagent to the ketone 8 (van Leusen & van Leusen, 1978).…”

Section: Chemistrymentioning

confidence: 99%

“…The synthesis of the cyclobutane 2-rimantadine analogues 25 and 26 is illustrated in Figure 3 and was accomplished by using cyclobutanone 22 as a starting material. This compound was prepared, according to a literature procedure (Bernaert et al, 1973), by the reaction of 2-adamantanone 4 with the tetrafluoroborate of the diphenylsulfonium cyclopropylide; the intermediate oxaspiropentane was rearranged to the cyclobutanone 22 upon treatment with HBF 4 . Raney-Ni hydrogenation of the ketone oxime 23 gave a mixture of products, due to hydrogenolysis of cyclobutane ring; in addition, its reductive amination using NaCNBH 3 resulted in the desired amine 25 in only 1% yield.…”

Section: Chemistrymentioning

confidence: 99%

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Are the 2-Isomers of the Drug Rimantadine Active Anti-Influenza a Agents?

Zoidis

Kolocouris

Foscolos

et al. 2003

Antivir Chem Chemother

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There is a lack of information in the medical chemistry literature concerning the anti-influenza A activity of the drug rimantadine's 2-isomer (2-rimantadine). We now present results showing that, although 2-adamantanamine (2-amantadine) 3 is only moderately active, some 2-rimantadine analogues are effective anti-influenza A virus agents in vitro. The 2-rimantadine analogues and their spirocyclobutane and spirocyclopentane congeners were synthesized through interesting routes. The 2-rimantadine analogues were 2-4 times more potent than rimantadine 2 against influenza virus A H2N2 strain; their spirocyclobutane congeners proved equally active to rimantadine 2. Two compounds exhibited a similar activity and one of the compounds was was fourfold more potent than rimantadine 2 against H3N2 strain.

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