Naslov
Tandem Diels-Alder-aza-Michael reaction - a new synthetic approach to rigid polycyclic guanidines

Autori
Barešić, Luka ; Glasovac, Zoran ; Margetić, Davor

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

Izvornik
8th EuChemS Chemistry Congress : Book of abstracts / Silva, Artur M. S. ; Galvão, Adelino M. ; Machado, Bruno F. ; Faria, Joaquim L. - Lisabon : Sociedade Portuguesa de Química, 2022, 461-461

ISBN
978-989-8124-35-7

Skup
8th EuChemS Chemistry Congress (ECC8)

Mjesto i datum
Lisabon, Portugal, 28.08.2022. - 01.09.2022

Vrsta sudjelovanja
Poster

Vrsta recenzije
Međunarodna recenzija

Ključne riječi
polycyclic guanidines ; oxanorbornanes ; cycloaddition

Sažetak
Oxanorbornane is bicyclic structural motif present in a variety of biological systems [1] and it can be used as glycomimetics [2], β-turn inducers [3], amphiphilic systems for drug delivery [4], etc. Such structures can be prepared by a variety of methods the main being cycloaddition/hydrogenation sequence starting from substituted furans [1]. This synthetic approach has a high atom economy and both of these steps in combination with easily available furan derivatives from biomass could be considered eco-friendly. Herein, we report synthesis of a series of novel guanidine substituted oxanorbornanes by the cycloaddition/hydrogenation sequence. A special emphasis is laid on a tandem reaction encompassing cycloaddition/aza-Michael intramolecular addition what results in a formation of novel polycyclic guanidines. Efficiency of the intramolecular reaction is discussed in terms of the structural difference of the starting furfuryl guanidines 3a-3f. To rationalize the experimental results, pKa values as well as the reaction mechanisms were investigated by the DFT computational approach.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA