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Design, synthesis and spectroscopic properties of crown ether-capped dibenzotetraaza[14]annulenes.

ABSTRACT: The first crown ether-capped dibenzotetraaza[14]annulenes (DBTAAs), featuring two macrocyclic binding sites fixed in a face-to-face orientation, were synthesized in satisfactory 26-28% isolated yields. Direct N-alkylation of 1,4,10-trioxa-7,13-diazacyclopentadecane by symmetric DBTAA derivatives bearing bromoalkoxy pendants proceed smoothly at a reasonable level of dilution (1.25 mM). The structures were fully characterized by HR-ESIMS, FTIR-ATR, 1H and 13C NMR spectroscopy and elemental analysis.

SUBMITTER: Zwolinski KM

PROVIDER: S-EPMC6423591 | biostudies-literature | 2019

REPOSITORIES: biostudies-literature

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Design, synthesis and spectroscopic properties of crown ether-capped dibenzotetraaza[14]annulenes.

Zwoliński Krzysztof Miroslaw KM Eilmes Julita J

Beilstein journal of organic chemistry 20190311

The first crown ether-capped dibenzotetraaza[14]annulenes (DBTAAs), featuring two macrocyclic binding sites fixed in a face-to-face orientation, were synthesized in satisfactory 26-28% isolated yields. Direct N-alkylation of 1,4,10-trioxa-7,13-diazacyclopentadecane by symmetric DBTAA derivatives bearing bromoalkoxy pendants proceed smoothly at a reasonable level of dilution (1.25 mM). The structures were fully characterized by HR-ESIMS, FTIR-ATR, <sup>1</sup>H and <sup>13</sup>C NMR spectroscopy ...[more]

PMID: 30931003

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