Naslov
Efficient synthesis of new of 17-, 18-, 19- and 20-membered N2O2-donor macrocycles by NaBH4 reduction

Autori
Paurević, Marija ; Dandić, Andrea ; Šrajer Gajdošik, Martina ; Vidović, Barbara ; Balić, Tomislav

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

ISBN
97896170780503

Skup
18th Blue Danube Symposium on Heterocyclic Chemistry

Mjesto i datum
Ljubljana, Slovenija, 18.09.2019. - 21.09.2019

Vrsta sudjelovanja
Poster

Vrsta recenzije
Međunarodna recenzija

Ključne riječi
synthesis, macrocycles, NaBH4 reduction, N2O2-donor

Sažetak
The oxa-aza macrocycles have been extensively studied due to their possible application as selective separating agents for toxic metal cations, chemical sensors and other. The affinity of macrocyclic system towards specific metal cation is governed by several tunable factors such as: ring size (cavity size), HSAB principle, conformation of donor atoms, flexibility of system etc. The poly-imine macrocycles are known to be rigid systems, due to the presence of C=N bond, and subsequently can be reduced to more flexible secondary amine by several different reduction agents (NaBH4, NaBH3CN, NaBH(OAc)3, H2). The reduction of an imine macrocycle to secondary amine macrocycle has been extensively used as intermediate step in preparation of pendant macrocycles, cryptands and spherands. Prior to this study we have developed relatively simple and efficient method for the preparation of 17- to 20-membered oxa-aza imine macrocycles by [1+1] cyclocondenzation reactions of appropriate dialdehydes and diamines. The obtained macrocycles were used as a starting material for the preparation of secondary amine analogues by NaBH4 reduction. The characterization of compounds was done by NMR and IR spectroscopy, elemental analysis and suitable crystals of 18-membered macrocycle were used for single crystal X-ray analysis. The results indicate significant changes in overall conformation of all synthesized macrocycles.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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