Part I: Nitroalkenes in the synthesis of heterocyclic compounds

Abstract

The applications of nitroalkenes in the synthesis of three-to five-membered O, N and S-heterocycles, including natural products are investigated in this review. These heterocyclic compounds were synthesized from nitroalkenes with a variety of substituents at the a and b-positions and those that were part of common and medium rings via a wide variety of reactions such as Michael addition reactions, epoxidation, [3 + 2] cycloaddition and many cascade/domino/tandem reactions. In addition, the potential of nitroalkenes to take part in multi-component and cascade reactions, particularly, in diastereo-and enantioselective versions is reviewed. The high reactivity of nitroalkenes and their potential to coordinate with the metal catalysts as well as organocatalysts signify them as efficient precursors in synthetic organic chemistry. Also, the flexibility of the nitro group in functional group manipulations has expanded the scope of the nitro group, in general, and nitroalkenes, in particular, in organic synthesis.

Design, preparation and characterization of Cu/GA/Fe3O4@SiO2 nanoparticles as a catalyst for the synthesis of benzodiazepines and imidazoles

“…Multicomponent reactions (MCRs) are powerful tools for the total synthesis of natural products, design and discovery of biologically active molecules and various heterocyclic compounds from simple and readily accessible starting materials. The atom economy of MCRs, their convergent character, operational simplicity and the structural diversity and complexity of the resulting molecules make this chemistry exceptionally useful for discovery and optimization processes in the pharmaceutical industry .…”

“…[4] These properties combined with the high accessibility of the globular arranged active sites of certain surface-modified Fe 3 O 4 @SiO 2 nanoparticles have encouraged their applications as supports for palladium and chiral ruthenium complexes, or organocatalysts such as 4-N,N-dimethylaminopyridine or proline. [8] Multicomponent reactions (MCRs) are powerful tools for the total synthesis of natural products, [9] design and discovery of biologically active molecules [10] and various heterocyclic compounds [11,12] from simple and readily accessible starting materials. The atom economy of MCRs, their convergent character, operational simplicity and the structural diversity and complexity of the resulting molecules make this chemistry exceptionally useful for discovery and optimization processes in the pharmaceutical industry.…”

An Efficient Four Component Domino Synthesis of Pyrazolopyranopyrimidines using Recyclable Choline Chloride:Urea Deep Eutectic Solvent

“…Facile and green synthetic approaches are important issues in organic synthesis. The generation of divergent and complicated molecules from either commercially available or readily accessible starting materials is an inspiring theme in contemporary organic synthesis . Meanwhile, multicomponent reactions are known as a powerful tool for the construction of novel and structurally complex molecules in a single pot ensuring high atom‐economy, good overall yields and high selectivity, lower costs, shorter reaction times, minimizing waste, labor, energy, and avoidance of expensive purification processes.…”

Metal-Free Synthesis of Indoles from Arylhydrazines and Nitroalkenes at Room Temperature

“…[10] High reactivity of the easily accessible nitroalkenes and flexibility of the nitro group signifies them as efficient precursors for the synthesis of N, O or S containing 3-5 membered heterocycles in bioactive molecules. [11] Recently, we have also developed several methodologies using nitroalkene as a coupling partner for the synthesis of various biologically active scaffolds like furans, imidazoles and imidazopyridines. [12] Now we explore the synthetic applicability of nitroalkenes as coupling partners with arylhydrazines for the direct synthesis of substituted indoles under ambient conditions (Scheme 1).…”