ChemInform Abstract: Synthesis of 1,3‐Bis[2‐(p‐nitrobenzylideneamino)ethyl]adamantane.

Popov, Yu. V.; Korchagina, T. K.; Chicherina, G. V.; Ermakova, T. A.

doi:10.1002/chin.200050084

ChemInform

2000

DOI: 10.1002/chin.200050084

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ChemInform Abstract: Synthesis of 1,3‐Bis[2‐(p‐nitrobenzylideneamino)ethyl]adamantane.

Yu. V. Popov¹,

T. K. Korchagina²,

G. V. Chicherina³

et al.

Abstract: ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

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“…Polyimides containing adamantane fragments are more hydrolytically and thermally stable. Highly efficient rubber stabilizers were obtained on the basis of 2,2′-(adamantane-1,3-diyl)diethanamine [14,15] [16]. 2,2′-(Adamantane-1,3-diyl)diethanamine is also added to epoxy resins to improve their optical properties and durability [17].…”

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Arylation of adamantanamines: III. Palladium-catalyzed arylation of adamantane-1,3-diyldimethanamine and 2,2′-(adamantane-1,3-diyl)diethanamine

et al. 2011

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Palladium-catalyzed arylation of adamantane-1,3-diyldimethanamine and 2,2′-(adamantane-1,3-diyl)diethanamine with isomeric bromochloro-and dibromobenzenes was studied. The yields of N,N′-diarylation products depend on the initial diamine and dihalobenzene structure. Side reactions were revealed, which reduced the yield of the target products. The arylation of 2,2′-(adamantane-1,3-diyl)diethanamine gives the corresponding N,N′-diaryl derivatives with better yield. The possibility for synthesizing unsymmetrical N,N′-diaryl derivatives of 2,2′-(adamantane-1,3-diyl)diethanamine was demonstrated. * For communication II, see [1].In the preceding communications [1, 2] we reported on the results of our studies on palladium-catalyzed arylation of adamantane-containing monoamines. The synthesis of nitrogen-containing macrocycles from 2,2′-(adamantane-1,3-diyl)diethanamine was described in [3,4]. Insofar as catalytic amination with participation of adamantane-containing amines is largely determined by the amine structure, we believed it reasonable to perform systematic study on palladium-catalyzed arylation of diamines of the adamantane series, which could give rise to wider diversity of N-aryl derivatives. Adamantane-1,3-diyldimethanamine and 2,2′-(adamantane-1,3-diyl)diethanamine were synthesized from the corresponding dicarboxylic acids through their chlorides, amides, and nitriles; the latter were reduced with lithium tetrahydridoaluminate in tetrahydrofuran with a yield of up to 63% [5,6]. Antiviral properties of adamantane-1,3-diyldimethanamine and 2,2′-(adamantan-1,3-diyl)diethanamine hydrochlorides were examined in [6], and the latter turned out to be active against bird influenza viruses.The applications of these amines are quite versatile. New carbocyclic Schiff bases were synthesized via reactions with aromatic aldehydes, and their biological activity was studied [7]. Stroganov et al. [8] studied specificity of vitrification of polymers upon hardening with diaminoadamantanes. Khardin and Pershin [9] proposed a procedure for the synthesis of diisocyanates by treatment of adamantane-containing diamine dihydrochlorides with phosgene. Diisocyanates are introduced into polymeric chain of polyurethanes to enhance their chemical resistance and photostability. Diamines of the adamantane series were used to synthesize polyamides that are characterized by higher heat resistance and hydrolytic stability than polymers based on adamantane-1,3-dicarboxylic acid [10]; moreover, polymers obtained from adamantane-1,3-diyldimethanamine showed a higher heat resistance than those derived from 2,2′-(adamantane-1,3-diyl)diethanamine. These diamines were also used to modify aromatic polyimides [11][12][13]. Polyimides containing adamantane fragments are more hydrolytically and thermally stable. Highly efficient rubber stabilizers were obtained on the basis of 2,2′-(adamantane-1,3-diyl)diethanamine [14,15]. For example, doping with such its derivatives as 1,3-bis[2-(m-fluorobenzylideneamino)ethyl]adamantane and 1,3-bis[2-(p-methoxybenz...

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Arylation of adamantanamines: III. Palladium-catalyzed arylation of adamantane-1,3-diyldimethanamine and 2,2′-(adamantane-1,3-diyl)diethanamine

et al. 2011

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“…Polyamides with enhanced hydrolytic and thermal stability were synthesized on the basis of compound I [11]. Chemical derivatives of diamine I have also found versatile applications; for example, the corresponding diisocyanates were introduced into polymeric chains of polyurethanes to improve their chemical stability and light resistance; addition of 1,3-bis(2-m-fluorobenzylideneaminoethyl)adamantane and 1,3-bis(2-m-methoxybenzylideneaminoethyl)adamantane improves mechanical properties of rubber [12]. Diamine I was also used to modify rubber [13,14].…”

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Palladium-catalyzed amination in the synthesis of macrocyclic compounds containing 1,3-disubstituted adamantane fragments

et al. 2009

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Palladium-catalyzed amination of 1,3-dibromobenzene, 2,6-dibromopyridine, 3,3′-dibromobiphenyl, 2,7-dibromonaphthalene, and 1,8-dichloroanthracene with an equimolar amount of 2,2′-(adamantane-1,3-diyl)diethanamine resulted in the formation of macrocyclic compounds containing one or several adamantane and one or several aromatic fragments. The reactions of 2,2′-(adamantane-1,3-diyl)diethanamine with excess 1,3-dibromobenzene, 2,6-dibromopyridine, 1,8-dichloroanthracene, and 1,8-dichloroanthraquinone gave the corresponding N,N′-diaryl derivatives. Polyaza macrocycles incorporating adamantane, aromatic, and 4,7,10-trioxatridecane-1,13-diamine fragments, were obtained by palladium-catalyzed amination of the N,N′-diaryl derivatives with 4,7,10-trioxatridecane-1,13-diamine.Thirty years ago Novikov et al.[1] proposed a convenient and reliable procedure for the preparation of 1,3-bis(2-aminoethyl)adamantane (I), and this compound was widely used in practice since that time. Diamine I, 1,3-bis(aminomethyl)adamantane, and the corresponding hydrochlorides were tested for antiviral activity [2], and the first of these turned out to be active against avian influenza [3], while the second was patented as antiviral drug for the treatment of domestic animals [4,5]. Diamine I is used as a component in the preparation of epoxide polymers [6] with a view to improve their optical parameters and endurance [7], as well as for modification of aromatic polyimides [8][9][10]. Polyamides with enhanced hydrolytic and thermal stability were synthesized on the basis of compound I [11]. Chemical derivatives of diamine I have also found versatile applications; for example, the corresponding diisocyanates were introduced into polymeric chains of polyurethanes to improve their chemical stability and light resistance; addition of 1,3-bis(2-m-fluorobenzylideneaminoethyl)adamantane and 1,3-bis(2-m-methoxybenzylideneaminoethyl)adamantane improves mechanical properties of rubber [12]. Diamine I was also used to modify rubber [13,14]. Cyclic Schiff base were synthesized from diamine I, and their biological activity was studied [15].Our interest in diamine I, as well as in other adamantane-containing diamines, is related to the possibility of their catalytic N-arylation to obtain new potential pharmacologically active compounds. We recently synthesized N,N′-dipyridyl derivative of 1,3-bis-(aminomethyl)adamantane, which showed nootropic effect in mice [16]. We believed that introduction of an adamantane fragment into polyaza macrocycles should enhance their lipophilicity and hence permeability through cell membranes. Therefore, we made an attempt to synthesize such macrocycles whose cavity be capable of transporting small organic molecules. Combination of adamantane and diaminoaryl fragments in a single molecule seems to be promising from the viewpoint of further biological studies. For example, diaminonaphthalenes exhibit versatile biological activity [17][18][19][20][21], diaminoanthraquinone derivatives were studied as anticarcinogenic agents [22], a...

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ChemInform Abstract: Synthesis of 1,3‐Bis[2‐(p‐nitrobenzylideneamino)ethyl]adamantane.

Cited by 2 publications

References 0 publications

Arylation of adamantanamines: III. Palladium-catalyzed arylation of adamantane-1,3-diyldimethanamine and 2,2′-(adamantane-1,3-diyl)diethanamine

Arylation of adamantanamines: III. Palladium-catalyzed arylation of adamantane-1,3-diyldimethanamine and 2,2′-(adamantane-1,3-diyl)diethanamine

Palladium-catalyzed amination in the synthesis of macrocyclic compounds containing 1,3-disubstituted adamantane fragments

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