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

作者信息

Katritzky Alan R., Belyakov Sergei A., Sorochinsky Alexander E., Steel Peter J., Schall Otto F., Gokel George W.

机构信息

Department of Molecular Biology and Pharmacology, Washington University School of Medicine, Washington University, St. Louis, Missouri 63110.

出版信息

J Org Chem. 1996 Oct 18;61(21):7585-7592. doi: 10.1021/jo961099o.

DOI:10.1021/jo961099o

PMID:11667692

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.

摘要