Abstract
Background: Benzofurans are very important structural motifs found in a great number of natural products and biologically active compounds. Many commercially available drugs, including citalopram, dronedarone, saprisartan, darifenacin, and galantamine are derived from benzofuran core entities. Due to the diversity of benzofuran derivatives in the therapeutic response profile, developing novel and truly efficient methods for their synthesis from low-cost and easily accessible starting materials in one-step has been the subject of number of papers in recent years.
Objective: Propargylic ethers are one of the most specific class of heteroatom-containing alkynes showing a large application as intermediates in organic synthesis. These compounds were successfully transformed into various organic compounds, including chromenes, carbazoles, cyclopentanones, 1, 2-dihydropyridines, α, β- unsaturated ketones, alcohols, allenes and many more. Synthesis of benzofurans via intramolecular cyclization of aryl propargyl ethers has become one of the most popular applications of theses versatile compounds. In this review we will highlight the recent discoveries and advances in this interesting research arena.
Method: The review is divided into two major sections. The first will discuss cyclization of ortho-halo aryl propargylic ethers, while the second focuses exclusively on cyclization of ortho-unsubstituted aryl propargyl ethers. It is should be mentioned that special emphasis is placed on the mechanistic aspects of these reactions.
Conclusion: Synthesis of benzofuran derivatives via intramolecular cyclization of corresponding aryl propargyl ethers have witnessed rapid and comprehensive development in recent years. The main advantages of this synthetic strategy include the use of simple, inexpensive, non-toxic, and readily accessible starting materials, and its pot, atom, and step economy.
Keywords: Aryl propargyl ethers, benzofurans, 2, 3-dihydrobenzofurans, 5-exo-dig cyclization, Palladium, cesium fluoride.
Graphical Abstract
Call for Papers in Thematic Issues
Exploring the Role of Chemical Graph Theory in Advancing Current Organic Synthesis
Organic synthesis is a fundamental discipline in chemistry, crucial for the creation of complex molecules with diverse applications in pharmaceuticals, materials science, and beyond. However, the process of designing efficient synthetic routes for target molecules remains challenging. Chemical graph theory, a branch of theoretical chemistry, offers powerful tools for understanding ...read more
Photoswitches for Molecular Recognition
This Special Issue would cover the hot topics on synthesis and chemical and photophysical characterization of new photoswitchable derivatives and their applications on molecular recognition of metabolites and biological active compounds, both in physiological medium and in living cells. Photoswitches are compounds that can change their conformation or properties in ...read more
Related Books
Advances in Organic Synthesis
The Synthetic Methods, Structures, and Properties of the Ca-C σ Bond Organocalcium Containing Compounds
Advances in Organic Synthesis
Chemistry of Bipyrazoles: Synthesis and Applications
Advances in Organic Synthesis
Advanced Nanocatalysis for Organic Synthesis and Electroanalysis
Advances in Organic Synthesis
Advances in Organic Synthesis
37
2
1
1