Ring‐Closing Metathesis: Novel Routes to Aromatic Heterocycles

Abstract

Olefin metathesis has been established as an important and general reaction in synthetic organic chemistry. Recently, it has attracted interest as a powerful tool for the construction of aromatic heterocycles. The importance of heteroaromatic motifs in medicinal chemistry and biology, as well as the efficiency and wealth of metathesis transformations, have resulted in significant success in this rapidly developing area.

One‐Pot Ring‐Closing Metathesis (RCM)/Oxidation by an Assisted Tandem Ruthenium Catalysis for the Synthesis of 2‐Quinolones

“…Therefore, the development of better synthetic approaches to 2-quinolones remains an active research area. [15] In this communication, we report an assisted tandem Ru catalysis system which promotes a onepot ring-closing metathesis [16] (RCM)/oxidation providing 2-quinolones. Although there are some related tandem reactions involving metathesis as the first step, [17] an oxidation involving CH 2 with modified Grubbs-type ruthenium complexes is unprecedented.…”

Natural product synthesis as a challenging test of newly developed methodology

“…68 Studies from our laboratories have focussed on developing both intramolecular variants (ring-closing metathesis (RCM) strategies) and intermolecular variants (crossmetathesis (CM) strategies) for the construction of a range of functionalized 5-and 6-membered heteroaromatic motifs. 69 6.1 Ring-closing metathesis strategies (À)-(Z)-Deoxypukalide: RCM for the construction of furans. We have recently described the development of a RCM approach for the synthesis of both furans and pyrroles (Scheme 24).…”

Synthesis of Heteroaromatic Compounds by Alkene and Enyne Metathesis

“…Methodologies that are based upon robust and operationally simple catalysis platforms are likely to be especially valuable. In this chapter, the rapidly expanding area of metathesis-based heteroaromatic methodologies is outlined [5][6][7][8]. This approach capitalises upon the combination of user-friendly ruthenium-based catalysts and readily available alkene substrates to provide regiocontrolled access to a wide range of heteroarene targets (Scheme 1).…”