Synthesis of macrocyclic compounds via consecutive Sonogashira – Ugi – Sonogashira reactions

Glavaš, Mladena; Gredičak, Matija; Jerić, Ivanka Synthesis of macrocyclic compounds via consecutive Sonogashira – Ugi – Sonogashira reactions. In: The 21st European Symposium on Organic Chemistry Book of abstracts (14 July 2019 - 18 July 2019) Vienna, Austria. (Unpublished)

PDF - poster Download (526kB)

Abstract

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.

Item Type:	Unpublished conference/workshop items or lecture materials
Uncontrolled Keywords:	multicomponent reactions; Ugi reaction; Sonogashira reaction
Subjects:	NATURAL SCIENCES > Chemistry > Organic Chemistry
Divisions:	Division of Organic Chemistry and Biochemistry NMR Center
Depositing User:	Mladena Glavaš
Date Deposited:	18 Dec 2025 15:07
URI:	http://fulir.irb.hr/id/eprint/10591

Actions (login required)

View Item