Synthesis of Olefinic Crown Diamides and their Conversion into Pyrazolino Macrocycles: Promising Photoluminescent Crown Compounds

Abstract

Macrocyclic crown diamides with 16- or 24-membered rings containing E- and Z-olefinic double bonds were synthesized either by bisalkylation or by ring-closing metathesis (RCM) techniques. The two methods were evaluated and compared with regard to yield and to product stereochemistry. Isomerization of some Z-olefinic macrocycles to their corresponding E-isomers was achieved using Grubbs’ catalyst second generation. Some of the required starting dials, diols and bishalo compounds were prepared by different routes including cross-metathesis (CM). The latter was compared with other investigated methods. Some of the olefinic macrocycles were subjected to cycloaddition reactions with diphenylnitrileimine to give the corresponding pyrazolino macrocycles. The latter showed interesting emission spectra.

Key words

ring-closing metathesis - E,Z isomerization - macrocyclic ether amides - cycloaddition - pyrazolino macrocycles

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