Novel Syntheses of N-Pivot Lariat Diaza-Crown Ethers from 4,13-Bis(benzotriazolylmethyl)-4,13-diaza-1,7,10,16-tetraoxacyclooctadecane

4,13-Bis(benzotriazolylmethyl)-4,13-diaza-1,7,10,16-tetraoxacyclooctadecane (6) was synthesized as a versatile intermediate in the preparation of bis(lariats) of diaza-18-crown-6. N,N‘-Bis(umbelliferon-8-ylmethyl) derivative 8, bis(lariats) with terminal unsaturated groups (11c,e), ester functionali...

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Veröffentlicht in:Journal of organic chemistry 1996-10, Vol.61 (21), p.7585-7592
Hauptverfasser: Katritzky, Alan R, Belyakov, Sergei A, Sorochinsky, Alexander E, Steel, Peter J, Schall, Otto F, Gokel, George W
Format: Artikel
Sprache:eng
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Zusammenfassung:4,13-Bis(benzotriazolylmethyl)-4,13-diaza-1,7,10,16-tetraoxacyclooctadecane (6) was synthesized as a versatile intermediate in the preparation of bis(lariats) of diaza-18-crown-6. N,N‘-Bis(umbelliferon-8-ylmethyl) derivative 8, bis(lariats) with terminal unsaturated groups (11c,e), ester functionalities (11d), N,N‘-di-β-aralkyl derivatives (11a,b), and γ-oxy-substituted (13, 14) and γ-amino-substituted (17−19) propylene-side-armed derivatives were thus prepared in moderate to excellent yields. The X-ray structure of bis(lariat) 6 and stability constants for several of the complexes of bis(lariats), derivatives of 6, with metal cations are discussed.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo961099o