ChemInform Abstract: SYNTHESE VON 2‐AMINOADAMANTAN UND N‐SUBSTITUIERTEN DERIVATEN

Lavrova, L. N.; Климова, Н. В.; Shmar'yan, M. I.; Ulyanova, Olga; Vikhlyaev, Yu. I.; Сколдинов, А. П.

doi:10.1002/chin.197426255

Cited by 4 publications

(6 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Commercially available isomeric bromochloro-and dibromobenzenes, sodium tert-butoxide, BINAP, DavePHOS, and Xanthphos were used without additional purification. Adamantan-1-amine (I) [36], adamantan-2-amine (XI) [37], and Pd(dba) 2 [38] were synthesized according to known methods (the latter was not recrystallized). Dioxane was distilled first over alkali and then over metallic sodium; CH 2 Cl 2 and MeOH were distilled.…”

Section: Methodsmentioning

confidence: 99%

Palladium-catalyzed amination of isomeric dihalobenzenes with 1- and 2-aminoadamantanes

et al. 2010

View full text Add to dashboard Cite

Palladium-catalyzed amination of isomeric bromochloro-and dibromobenzenes with 1-and 2-aminoadamantanes was studied. The best yields of the corresponding monoamination products were obtained in the reactions of 2-aminoadamantane with bromochlorobenzenes. The arylation of 1-aminoadamantane was successful in the presence of donor phosphine ligand. The amination of o-and m-dibromobenzenes was strongly complicated by formation of diamination products. Conditions ensuring predominant formation of the latter were found. The arylation of 2-aminoadamantane was accompanied by oxidation of the initial amine and reduction of aryl halide.Adamantane is one of the simplest cage-like hydrocarbons, which attracts researchers' attention over a period of more than 50 years. Up to now, thousands compounds containing an adamantane fragment have been synthesized and studied, and many of them have found applications in various fields of practice, primarily as physiologically active substances. Aminoadamantanes and their derivatives are especially interesting as potential medicines; for example, adamantan-1-amine hydrochloride (amantadine) turned out to be effective in the treatment of Parkinson's disease [1,2] and was also used in the treatment of hepatitis C [3]. 1-(1-Adamantyl)ethanamine (rimantadine) [4] is widely used as antiviral agent, memantine (derivative with two amino groups) [5] is an N-methyl D-aspartate receptor antagonist; many other drugs have more complex structures and often contain aromatic fragments; examples are chlodantane (immunostimulant) [6], ladasten (neurostimulator) [7], etc. Most publications deal with adamantan-1-and -2-amine derivatives possessing an amide group; many hundreds of such compounds have already been reported. In the recent years, successful biological tests have been performed with various N-aryl-and N-hetarylaminoadamantanes, including those containing halogen atoms (fluorine, chlorine, bromine) in the aromatic substituent. Therefore, we set ourselves the task of developing a convenient procedure for the synthesis of a new family of N-haloaryl-substituted adamantanamines with a view to subsequently test them for biological activity.There are hundreds publications on the synthesis and applications of adamantan-1-amine; however, published data on the synthesis of its N-aryl derivatives are very scanty. Olifirov et al. [8] synthesized N-phenyladamantan-1-amine in 51% yield from adamantan-1-ol and aniline in the presence of aniline hydrochloride or aluminum anilide hydrochloride. In the early publication by Kogay and Sokolenko [9], the use of 1,3-dehydroadamantane was described: this compound reacted with aniline in the presence of aniline hydrochloride to produce a mixture of aniline alkylation products at the nitrogen atom and at the para-position at a ratio of 4 : 1. N-(1-Adamantyl)aniline was isolated in 55% yield. Stepanov and Stolyarov [10] synthesized N-(1-adamantyl)aniline by alkylation of aniline with 1-bromoadamantane. The reaction occurred under severe conditions and involved the nit...

show abstract

Section: Methodsmentioning

confidence: 99%

Palladium-catalyzed amination of isomeric dihalobenzenes with 1- and 2-aminoadamantanes

et al. 2010

View full text Add to dashboard Cite

show abstract

“…2-( N -Methylamino)adamantane. This known amine was obtained by reducing the imine 4 -H (50 mg, 0.31 mmol) with sodium borohydride (0.46 mg, 1.2 mmol, in four portions) in methanol (2.0 mL) during 20 min. Stirring was continued for 6 h. The pH was adjusted to 1 with concentrated hydrochloric acid to decompose unreacted borohydride and then to 12 with concentrated sodium hydroxide to liberate the amine.…”

Section: Methodsmentioning

confidence: 99%

“…Stirring was continued for 6 h. The pH was adjusted to 1 with concentrated hydrochloric acid to decompose unreacted borohydride and then to 12 with concentrated sodium hydroxide to liberate the amine. After evaporation to dryness, the amine was isolated by extraction of the residue with ether and evaporation of solvent to give a white solid (46 mg, 91%); mp 86 °C, lit . 87 °C.…”

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Effects of Substituent Modification on Face Selection in Reduction

Kaselj

Salvatore

et al. 1998

J. Org. Chem.

View full text Add to dashboard Cite

“…By the Leuckart reaction from the adamantanone with 1-or 2-aminoadamantane in severe conditions [11,12] the corresponding diadamantylamines were obtained. No published data exist on the synthesis of any other diframework amines.…”

mentioning

confidence: 99%

Selective reductive dimerization of homocubane series oximes

et al. 2011

View full text Add to dashboard Cite

The mixture of di-and monoethylene ketals obtained by the reaction of 1,9-dibromopentacyc lo[5.4.0.0 2,6 .0 3,10 .0 5,9 ]-undeca-8,11-dione followed by hydrolysis and ring contraction by Faworsky method was converted into a mixture of ethylene ketals of 7-bromopentacyclo[5.3.0.0 2,5 .0 3,9 .0 4,8 ]decan-6-one-4-and 5-bromopentacyclo[5.3.0.0 2,5 .0 3,9 .0 4,8 ]decan-6-one-8-carboxylic acid where the carboxy group was replaced by bromine along the procedure of Hunsdiecker-Borodine-Cristol. 6-Ethylene ketal of the pentacyclo[5.3.0.0 2,5 .0 3,9 .0 4,8 ] decan-6-one obtained by the debromination of ethylene ketals of 4,7-and 5,8-dibromopentacyclo[5.3.0.0 2,5 .0 3,9 .0 4,8 ] decan-6-one was hydrolyzed to ketone whose oxime was selectively reduced on a platinum catalyst into the di-6-pentacyclo[5.3.0.0 2,5 .0 3,9 .0 4,8 ]decylamine. The reaction of reductive dimerization was also characteristic of pentacyclo[4.3.0.0 2,5 .0 3,8 .0 4,7 ]-nonan-9-one and pentacyclo[6.3.0.0 2,6 .0 3,10 .0 5,9 ]undecan-4-one oximes, whereas the composition of the reduction products of pentacyclo[5.4.0.0 2,6 .0 3,10 .0 5,9 ]undecan-8-one oxime depended on the amount of the catalyst.

show abstract

ChemInform Abstract: SYNTHESE VON 2‐AMINOADAMANTAN UND N‐SUBSTITUIERTEN DERIVATEN

Abstract: Durch fünfstündiges Erhitzen des Adamantanons (I) mit den Aminen (II) und 98%iger Ameisensäure (Molverhältnis wie l 22:2) auf 130‐1 50°C und Aufarbeitung des Reaktionsgemisches mit siedendem konz. HCl lassen sich glatt die Aminoadamantane (III) (als Hydrochloride) darstellen.

Cited by 4 publications

References 0 publications

Palladium-catalyzed amination of isomeric dihalobenzenes with 1- and 2-aminoadamantanes

Palladium-catalyzed amination of isomeric dihalobenzenes with 1- and 2-aminoadamantanes

Effects of Substituent Modification on Face Selection in Reduction

Selective reductive dimerization of homocubane series oximes

Contact Info

Product

Resources

About