Synthesis of Macrocycles Containing Endocyclic Chiral BINAM Moieties

Abstract

'-бинафталин-2,2'-диамина (БИНАМ) и N,N'-ди(3-бромфенил) замещенного оксадиамина и из N,N'-ди(3-бромфенил)

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

“…[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.…”

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

“…[24] This method allowed to synthesize macrocycles with phenylene, naphthalene and benzyl spacers. Introduction of the 1,8-or 1,5-diaminoanthraquinone moiety in the macrocycle is useful for the construction of colorimetric chemosensors, as it was shown by us previously.…”

“…After evaporating the solvent, target compounds were isolated by column chromatography as deep-red solids using a sequence of eluents: CH 2 Cl 2 , CH 2 Cl 2 /MeOH 200:1 -50: 1. 11,21,22,23,24,26,27,28,29,31,32,33,34,17:38, [1,26,5,11,16,22] J=8.9 Hz), 10.86 (2H, s), two NH protons were not unambiguously assigned. 13 Macrocycle 13.…”

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

“…Pd(dba) 2 was synthesized using a known procedure [45]. N,N -di(3-bromophenyl)-substituted (S)-BINAM 2 was obtained by a described method [41]. Compound 8.…”

“…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.…”