Recent Advances of Michael/hetero‐Michael Addition Reaction in the Synthesis of 3‐Nitro‐2H‐chromene Derivatives

Abstract

3‐Nitro‐2H‐chromene and derivatives are the significant structural building blocks of many natural products and pharmacologically active compounds. So, great deals of effort have been made for the development and improvement of 3‐nitro‐2H‐chromene functionalized scaffolds by utilizing different methodologies. Among the various strategies, Michael/hetero‐Michael addition reactions to 3‐nitro‐2H‐chromene have been established as the most vibrant and unique research area for the construction of diverse C−C and C−X (X=heteroatoms) bonds providing versatile 2H‐chromene frameworks. In recent years, a broad range of efficient Michael donors has been explored extensively which motivates the scientific community to work on these useful 2H‐chromene frameworks in presence of different bases, transition metals, organocatalysts, and base/catalyst‐free conditions. Considering the importance of this research field, the present review highlights the major advancements of Michael/hetero‐Michael addition reaction to 3‐nitro‐2H‐chromenes utilizing various Michael donors from the year 2010 to 2022 in a comprehensive manner.

Base catalyzed one-pot thia-Michael addition-oxidation reaction of hetero-aromatic thiols to 2-aryl-3-nitro-2H-chromenes and their antibacterial evaluation

“…As such, owing to these unique biological and pharmacological characteristics, we explored the Michael addition of sulfur–nitrogen-containing heterocyclic scaffolds with medicinally active 2-aryl-3-nitro-2 H -chromene derivatives. 17,18 Note that our group has already reported aza/carba-Michael addition reactions with 3-nitro-2 H -chromene derivatives and examined the antibacterial properties. 19–21 In 2017, Yang et al were the first to report a DCM-mediated catalyst-free sulfa Michael addition reaction involving heteroaromatic thiols and aliphatic nitrostyrene.…”

Kinetic Resolution of a Planar–Chiral [2.2]Paracyclophane via Michael Addition to Nitroolefins Catalyzed by N‐Terminal Guanidinylated Helical Peptide

“…Over the past few decades, numerous research groups have published studies on this reaction, exploring different Michael donors and catalyst recognition modes [3–7] . These endeavors have provided a wealth of important precursors for natural products and bioactive compounds [8,9] . In this regard, our group has recently reported the peptide–catalyzed asymmetric conjugate addition of β‐dicarbonyl compounds to nitroolefins (Scheme 1a) [10] .…”

Domino Conjugate Addition-1,4-Aryl Migration for the Synthesis of α,β-Difunctionalized Amides

“…To circumvent these limitations, we envisaged a universal ionic Truce–Smiles rearrangement protocol using pronucleophiles in a conjugate addition to directly generate α,β-difunctionalized amides from sulfonyl acrylimides (Scheme D) . In contrast to the radical initiation, the ionic Truce–Smiles rearrangement with extrusion of SO 2 is often restricted to electron-deficient aryl systems. ,, On the other hand, ionic conjugate addition can be achieved with a wide range of nucleophiles, − including various carbon-, sulfur-, phosphorus-, and most noteworthily, nitrogen-nucleophiles, which would enable access to a diverse range of β-amino amides. Herein, we report our key findings in this domino conjugate-addition-initiated aryl migration featuring the unprecedented ability of sulfonyl imides to transfer electron-neutral aromatic moieties by polar Truce–Smiles rearrangement.…”