Hetero-Diels-Alder Reactions in the Synthesis of Biologically Active Nitrogen Compounds: A Review

Abstract

Background: The Hetero-Diels-Alder reaction (HDAR) is a method extensively used in organic chemistry as a tool in the synthesis of innumerous polycyclic compounds in particular nitrogen compounds, presents in many natural products, medicinally relevant substances and organic materials. The literature describes innumerable studies of HDAR using classic methods and modern developments such as reactions on the solid phase, the use of catalysts, transformations in aqueous solution and under microwaves. Objective: This review describes a variety of HDAR focused on obtaining nitrogen-containing compounds of considerable chemical and biological interest, and highlighting reported biological activity. Conclusion: This review has shown the importance of the HDA reaction as a tool of organic chemistry in the synthesis of nitrogen compounds. This type of reaction presents important properties including bond-forming economy, high regio- and stereoselectivities and thus provides highly efficient routes to access a wide range of polycyclic compounds. In addition to the variety of nitrogen compounds synthetized successfully by this method, they present relevant biological properties.

New Dimensions in Rongalite Chemistry: The Land of Opportunities in Organic Synthesis and Material Sciences

“…A pericyclic [4+2]‐cycloaddition protocol is a powerful tool and has been continuously used by the synthetic organic chemists for the generation of diverse medicinally active molecules. Since its finding in 1928 (Nobel Prize 1950) in the laboratory of Otto Diels, its applications in organic synthesis is growing exponentially day‐by‐day, and to my best knowledge almost every architecturally complex natural or non‐natural products involve this powerful tool at some stage to showcase the target molecules . In this context, a variety of dienes and dienophiles either commercially available or easily prepared have been employed in DA‐reaction .…”

Recent Applications of the Diels–Alder Reaction in the Synthesis of Natural Products (2017–2020)

“…In 2018 Yang and Gao reviewed the Diels-Alder reaction of ortho-quinone methide-derivatives with various electrophiles for the scope of total syntheses, emphasizing the versatility and broad scope of the protocol 10,11 and Andre et al described several hetero-variants in the synthesis of polycyclic natural products. 12 With this review, we want to highlight selected Diels-Alder reactions of the years 2017 to 2020 which provide new strategies and tactics for the total synthesis of natural products. Furthermore, novel synthesis-relevant methodologies were also selected and presented herein.…”

“…10,11 Meanwhile, Lacerda et al described several hetero variants for the synthesis of polycyclic natural products. 12 In this short review, we endeavor to highlight selected Diels-Alder reactions reported in the literature between 2017 and 2020 that provide new strategies and tactics for…”

“…10 11 Meanwhile, Lacerda et al described several hetero variants for the synthesis of polycyclic natural products. 12…”

First thia-Diels–Alder reactions of thiochalcones with 1,4-quinones

“…Hetero-Diels–Alder reactions are considered to be a powerful methodology widely explored for the synthesis of six-membered heterocycles [1–2] with numerous applications for the construction of complex molecules including naturally occurring products [3–4], drugs [5–6], agrochemicals [7], etc. In addition, asymmetric hetero-Diels–Alder reactions are of current interest [8–10].…”