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

Glavaš, Mladena; Jerić, Ivanka Synthesis of macrocyclic compounds via consecutive Sonogashira-Ugi-Sonogashira reactions. In: The 3rd Mini Symposium of Medicinal and Pharmaceutical Chemistry for Young Scientist (12 November 2019 - 12 November 2019) Zagreb, Hrvatska. (Unpublished)

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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 the most utilized isocyanide-based multicomponent reactions (IMCRs) which provides a rapid coupling of an aldehyde, an amine, a carboxylic acid and an isocyanide affording -acylaminoamides [3]. Compounds with 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Unpublished conference/workshop items or lecture materials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:

Sonogashira reaction; multicomponent reactions; Ugi reaction; cyclization

Subjects:

NATURAL SCIENCES > Chemistry > Organic Chemistry

Divisions:

Division of Organic Chemistry and Biochemistry
NMR Center

Projects: