Chiral BINAM-Containing Macrocycles with Endocyclic 1,8- and 1,5-Disubstituted Anthraquinone Structural Fragments

Grigorova, O. K.; Averin, Alexei D.; Maloshitskaya, O. A.; Beletskaya, I. P.

doi:10.6060/mhc170937a

Cited by 9 publications

(4 citation statements)

References 25 publications

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“…[17][18][19] We began our own investigations aimed at the synthesis of BINAMcontaining macrocycles and their use in fluorescent enantioselective detection of amino alcohols. [20][21][22] The present work deals with the synthesis of cryptands on the basis of tetraazamacrocycles comprising endocyclic BINAM moiety.…”

Section: Introductionmentioning

confidence: 99%

Chiral Cryptands Possessing Tetraazamacrocyclic and BINAM Moieties: Synthesis and Evaluation as Fluorescent Detectors

Grigorova¹,

Averin²,

Maloshitskaya³

et al. 2019

MHC

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Сatalyzed amination of N,N'-di(bromobenzyl) substituted tetraazamacrocycles (cyclen, cyclam) with (S)-2,2'diamino-1,1'-binaphthalene (BINAM) was employed for the synthesis of a novel type of chiral cryptands. Better yields were obtained for cyclen derivatives. The compounds were modified with dansyl groups to enhance their fluorescent properties. Cryptands theirselves and their dansyl derivatives were evaluated for sensing enantiomers of 7 amino alcohols and 21 metal cations.

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Section: Introductionmentioning

confidence: 99%

Chiral Cryptands Possessing Tetraazamacrocyclic and BINAM Moieties: Synthesis and Evaluation as Fluorescent Detectors

Grigorova¹,

Averin²,

Maloshitskaya³

et al. 2019

MHC

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“…2,7-Dibromonaphthalene (1) was introduced into the catalytic amination with other chiral amines, such as the (S)-N-tert-butoxycarbonyl derivative of 2-(aminomethyl)pyrrolidine ( 12), (1S,2S)-2-(benzyloxy)cyclopentaneamine (14), and the (S)-N-tert-butoxycarbonyl derivative of (aminomethyl)piperidine ( 16) (Scheme 2). In all cases, the same Pd(dba) 2 /DavePhos catalytic system (10-12 mol.%) was utilized.…”

Section: Resultsmentioning

confidence: 99%

“…12 We also performed research along this line using the BINOL analog, 2,2´-diamino-1,1´-binaphthalene. [13][14][15] In this study we employed a procedure developed previously for the preparation of diamino derivatives of naphthalene 16 and synthe-Russ. Chem.…”

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confidence: 99%

Synthesis of optically active 2,7-disubstituted naphthalene derivatives and evaluation of their enantioselective recognition ability

et al. 2020

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The palladium-catalyzed amination was used to synthesize 2,7-diamino derivatives of naphthalene containing two chiral substituents and fl uorophore groups (dansyl, 7-methoxycoumarin, 6,7-dimethoxycoumarin, 6-aminoquinoline). The synthesized compounds were studied by UV absorption and fl uorescence spectroscopy in the presence of individual enantiomers of amino alcohols and salts of 21 metals. The possibility of using these compounds as fl uorescent detectors for optically active compounds and metals was examined. In the presence of (S)-leucinol, the diquinoline derivative showed enhanced emission with a maximum at shorter wavelengths, which is not typical of its (R) isomer. This fact can be used for the recognition of these enantiomers. A number of naphthalene derivatives can be considered as potential fl uorescent chemosensors for Cu II cations due to the total fl uorescence quenching in the presence of this metal.

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“…Taking this fact into consideration, we decided to develop the synthesis of BINAM-containing detectors using palladium-catalyzed amination reactions, which have become a powerful tool for creating C(sp 2 )-N bonds in last two decades [35][36][37]. Earlier, we acquired good experience in the synthesis of macrocyclic Compounds with the help of this catalytic reaction [38][39][40], and recently, we showed the possibility of introducing endocyclic BINAM moieties in macrocyclic Compounds using this approach [41][42][43][44]. We began the investigation of the detecting abilities of the macrocyclic Compounds using individual enantiomers of 1,2-amino alcohols due to some advantages of these model Compounds: Good solubility in organic solvents, their non-ionic nature, and the presence of two different donor atoms able to form hydrogen bonds.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Evaluation of the (S)-BINAM Derivatives as Fluorescent Enantioselective Detectors

Shaferov

Malysheva

Averin

et al. 2020

Sensors

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Pd(0)-catalyzed amination was employed for the synthesis of a new family of (S)-1,1′-bianaphthalene-2,2′-diamine derivatives possessing additional chiral and fluorophore substituents. The Compounds thus obtained were tested as potential detectors of seven amino alcohols, and some of them were found to be able to recognize individual enantiomers of certain amino alcohols by specific changes of their emission spectra in the presence of these analytes. A pronounced dependence of the detecting abilities on the nature of the substituents in the (S)-BINAM derivatives was observed.

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Chiral BINAM-Containing Macrocycles with Endocyclic 1,8- and 1,5-Disubstituted Anthraquinone Structural Fragments

Cited by 9 publications

References 25 publications

Chiral Cryptands Possessing Tetraazamacrocyclic and BINAM Moieties: Synthesis and Evaluation as Fluorescent Detectors

Chiral Cryptands Possessing Tetraazamacrocyclic and BINAM Moieties: Synthesis and Evaluation as Fluorescent Detectors

Synthesis of optically active 2,7-disubstituted naphthalene derivatives and evaluation of their enantioselective recognition ability

Synthesis and Evaluation of the (S)-BINAM Derivatives as Fluorescent Enantioselective Detectors

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