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Current Organic Synthesis

Editor-in-Chief

ISSN (Print): 1570-1794
ISSN (Online): 1875-6271

Review Article

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

Author(s): Andre F. Constantino, Carla S. Francisco, Diana C. Cubides-Roman and Valdemar Lacerda Jr.*

Volume 15, Issue 1, 2018

Page: [84 - 104] Pages: 21

DOI: 10.2174/1570179414666170517170230

Price: $65

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.

Keywords: Hetero-Diels-Alder reaction, cycloaddition, nitrogen compounds, synthetic methods, biological activity, medicinal chemistry.

Graphical Abstract

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