Halogenation of adamantane and related compounds

McKervey, M. Anthony; Grant, D. W.; Hamill, H.

doi:10.1016/s0040-4039(01)98131-6

Cited by 11 publications

(2 citation statements)

References 10 publications

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“…6,7-exo-Trimethylenebicyclo[3.2.1]octane (exo-2), together with 4-homoisotwistane (tricyclo [5.3.l.O3-8]undecane) (9)6_8>1°and homoadamantane, was discovered by us8 to be an intermediate in adamantane rearrangements of exo-1 and 2,3-trimethylenebicyclo[2.2.2]octane (3). 11 Here again, no 6,7-endo-trimethylenebicyclo[3.2.1]octane (endo-2) was detected during the rearrangement, suggesting a high reactivity of endo-2.…”

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confidence: 96%

Large enhancement of apparent isomerization rates in endo vs. exo precursors for trifluoromethanesulfonic acid catalyzed tricycloundecane rearrangements

Takaishi¹,

Inamoto²,

Aigami³

et al. 1975

J. Org. Chem.

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mentioning

confidence: 96%

Large enhancement of apparent isomerization rates in endo vs. exo precursors for trifluoromethanesulfonic acid catalyzed tricycloundecane rearrangements

Takaishi¹,

Inamoto²,

Aigami³

et al. 1975

J. Org. Chem.

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“…Amines (14 and 1736) were prepared from 13 (R = R' = H) and 15, respectively. Acylation of 17 led to amides 18.36 Similarly, 1-adamantanecarboxylic acid (19)7 gave novel esters (22)37 of polyhydric alcohols. The amidine (23)38 from 19 via acid chloride,15 amide,39 and nitrile40 reacted with malonic esters or cyanoacetic esters to give 2-(1 -adamantyl)pyrimidines (24).…”

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confidence: 99%

Biologically active polycycloalkanes. 1. Antiviral adamantane derivatives

Aigami¹,

Inamoto²,

Takaishi³

et al. 1975

J. Med. Chem.

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Convenient methods for the synthesis of 1-substituted 3-adamantyl chlorides and bromides (2), 1-adamantylphenols and -cresols (3), and 1-adamantylacetic (6) as well as 1,3-adamantanediacetic (11) acids are described. Several novel derivatives were synthesized from these key intermediates: adamantylcyclohexanols (4) and -cyclohexanones (5) from adamantylphenols (3), and esters (7,12, and 22), amides (13 and 18), thioamides (9 and 16), amidine (10), nitrile (15), and amines (14 and 17) from 1-adamantanecarboxylic (19) and -acetic (6) acids and 1,3-adamantanediacetic acid (11). Some adamantylpyrimidines (24) and -purines (25 and 26) were also prepared. Antiviral activities of the compounds obtained in this work and a series of new 1-adamantyl alkyl ketones synthesized before, together with those of some known adamantane derivatives, were tested in vitro on monolayer culture of chick ambryo fibroblasts against Newcastle disease virus.

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