Naslov
Synthesis of macrocyclic compounds via consecutive Sonogashira-Ugi-Sonogashira reactions

Autori
Glavaš, Mladena ; Gredičak, Matija ; Jerić, Ivanka

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, neobjavljeni rad, ostalo

Skup
The 21st European Symposium on Organic Chemistry

Mjesto i datum
Beč, Austrija, 14.07.2019. - 18.07.2019

Vrsta sudjelovanja
Poster

Vrsta recenzije
Nije recenziran

Ključne riječi
macrocyclic compounds ; multicomponent reactions ; Sonogashira reaction ; Ugi reaction

Sažetak
Multicomponent reactions (MCRs) are among the most important reactions in organic synthesis [1, 2]. The main advantages of MCRs are rapid, cost-effective and sustainable access to chemical diverse small–molecule libraries from relatively simple and inexpensive components. The Ugi reaction is one of the most important isocyanide-based multicomponent reactions (IMCRs) and provides a rapid coupling of an aldehyde, an amine, a carboxylic acid and an isocyanide [3]. Compounds with the enediyne structural motif were isolated from natural products and showed strong anticancer activity [4]. Apart from their biological profile, enediyne compounds are widely utilized as structural motifs in material chemistry, catalysts design [5], and in metal complexation studies [6]. Our aim was to exploit enediyne structural rigidity in the synthesis of conformationally pre-defined macrocyclic compounds. Our strategy relies on functionalization of 1, 2- diiodobenzene [7] and subsequent Sonogashira reaction to yield different Ugi compounds a. The second Sonogashira reaction followed by the intramolecular cyclisation afforded highly decorated macrocyclic compounds b.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA