Monocyanomethylated thiacalix[4]arenes: synthesis and lower rim modification

Ковалев, В. В.; Khomich, E. V.; Shokova, E. A.; Luzikov, Yurij

doi:10.3998/ark.5550190.0009.404

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Cited by 4 publications

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“…Adamantane-1,3-diol is known [19,20] to act as a bi electrophile in the adamantylation of carbon-and nitrogen-centered nucleophiles in TFA; however, the use of more available and cheaper 1,3-dibromoadaman- tane for this purpose seemed more attractive. We previously showed that 1-bromoadamantane in boiling TFA is quantitatively converted to adamantan-1-yl trifluoroacetate and that it can be used for the adamantylation of various nucleophiles [21].…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Adamantylated Salicylic Acids

Shokova

Ковалев

2021

Russ J Org Chem

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5-[3(4)-R-Adamantan-1-yl]salicylic acids [R = H, Alk, Ar, OH, NHC(S)NH 2 ] have been synthesized by electrophilic substitution reactions of hydroxy-and bromoadamantanes with salicylic acid, as well as by reactions of 5-(3-hydroxyadamantan-1-yl)salicylic acid with carbon and nitrogen nucleophiles, in trifluoroacetic acid. The possibility of selective hydroxylation of the adamantane fragment in 5-(adamantan-1-yl)salicylic acid with sulfuric acid in trifluoroacetic anhydride has been demonstrated.

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Section: Resultsmentioning

confidence: 99%