Novel Syntheses of N-Pivot Lariat Diaza-Crown Ethers from 4,13-Bis(benzotriazolylmethyl)-4,13-diaza-1,7,10,16-tetraoxacyclooctadecane
- 1 January 1996
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 61 (21) , 7585-7592
- https://doi.org/10.1021/jo961099o
Abstract
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.Keywords
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