title: Novel Syntheses of N-Pivot Lariat Diaza-Crown Ethers from 4,13-Bis(benzotriazolylmethyl)-4,13-diaza-1,7,10,16-tetraoxacyclooctadecane.
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-beta-aralkyl derivatives (11a,b), and gamma-oxy-substituted (13, 14) and gamma-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.
authors.affiliation: Department of Molecular Biology and Pharmacology, Washington University School of Medicine, Washington University, St. Louis, Missouri 63110.
authors.forename: Alan R.
authors.initials: AR
authors.lastname: Katritzky
authors.forename: Sergei A.
authors.initials: SA
authors.lastname: Belyakov
authors.forename: Alexander E.
authors.initials: AE
authors.lastname: Sorochinsky
authors.forename: Peter J.
authors.initials: PJ
authors.lastname: Steel
authors.forename: Otto F.
authors.initials: OF
authors.lastname: Schall
authors.forename: George W.
authors.initials: GW
authors.lastname: Gokel