Construction of Functionalized (Dihydro)thieno[2,3-c]chromene Derivatives via a Domino Michael Addition/Intramolecular 
Cyclization Reaction

Yu, Li‐Si‐Han; Dong, Jian-Lian; Gao, Zhi-Jian; Wang, Jing; Xie, Jian‐Hua

doi:10.1055/s-0036-1591758

Cited by 7 publications

References 2 publications

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K₃PO₄–Mediated Synthesis of Chromeno–[3,4‐c]isoxazole from 3–Nitro–2H–chromene and α–Chloro Aldehyde via Michael Addition/C−Cl Bond Cleavage/Deformylation as Key Fragmentation Sequences

Pratap,

Shukla,

Giri

et al. 2024

Adv Synth Catal

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Here we report a transition metal– and oxidant–free annulation cascade method for the synthesis of chromeno–isoxazoles. The annulation reaction involves easily accessible starting materials, 3‐nitro‐2H‐chromene and α‐chloro aldehyde, yielding the structurally intriguing framework, chromeno[3,4‐c]isoxazoles employed by tripotassium phosphate as a base. The isoxazole ring construction over the 2H–chromene unit is believed to occur via a series of multiple reaction sequences. Here, the enolate generation/Michael addition/C–Cl bond cleavage/oxy–anionic addition to reactive tethered‐aldehyde/deformylation via retro– C–C and N–O bond cleavages are the most possible sequences which furnish the desired end–product in good chemical yields. The multiple reaction sequences occur in one‐pot at mild conditions, supported by experimental results and a few control experiments including DFT studies. This process exhibits a broad substrates scope illustrating good functional group compatibility towards both the nitrochromenes and aldehydes, and thus prove to be a general and efficient protocol for the synthesis of chromeno[3,4–c]isoxazoles. Overall, the use of nitrochromene as the limiting reagent, noteworthy functional group tolerance, scalability including great applications like chiral pool strategy towards the synthesis of enantioenriched chromeno‐isoxazole are the additional features.

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K₃PO₄–Mediated Synthesis of Chromeno–[3,4‐c]isoxazole from 3–Nitro–2H–chromene and α–Chloro Aldehyde via Michael Addition/C−Cl Bond Cleavage/Deformylation as Key Fragmentation Sequences

Pratap,

Shukla,

Giri

et al. 2024

Adv Synth Catal

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

et al. 2023

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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.

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[3+2] Annulation of 2-substituted 3-nitro-2H-chromenes with mercaptoacetaldehyde: stereoselective synthesis of tetrahydro-4H-thieno[3,2-c]chromen-3-ols

Barkov

Кочнев

Simonov

et al. 2021

Chem Heterocycl Comp

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Construction of Functionalized (Dihydro)thieno[2,3-c]chromene Derivatives via a Domino Michael Addition/Intramolecular Cyclization Reaction

Cited by 7 publications

References 2 publications

K₃PO₄–Mediated Synthesis of Chromeno–[3,4‐c]isoxazole from 3–Nitro–2H–chromene and α–Chloro Aldehyde via Michael Addition/C−Cl Bond Cleavage/Deformylation as Key Fragmentation Sequences

K₃PO₄–Mediated Synthesis of Chromeno–[3,4‐c]isoxazole from 3–Nitro–2H–chromene and α–Chloro Aldehyde via Michael Addition/C−Cl Bond Cleavage/Deformylation as Key Fragmentation Sequences

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

[3+2] Annulation of 2-substituted 3-nitro-2H-chromenes with mercaptoacetaldehyde: stereoselective synthesis of tetrahydro-4H-thieno[3,2-c]chromen-3-ols

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Construction of Functionalized (Dihydro)thieno[2,3-c]chromene Derivatives via a Domino Michael Addition/Intramolecular Cyclization Reaction

Cited by 7 publications

References 2 publications

K3PO4–Mediated Synthesis of Chromeno–[3,4‐c]isoxazole from 3–Nitro–2H–chromene and α–Chloro Aldehyde via Michael Addition/C−Cl Bond Cleavage/Deformylation as Key Fragmentation Sequences

K3PO4–Mediated Synthesis of Chromeno–[3,4‐c]isoxazole from 3–Nitro–2H–chromene and α–Chloro Aldehyde via Michael Addition/C−Cl Bond Cleavage/Deformylation as Key Fragmentation Sequences

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

[3+2] Annulation of 2-substituted 3-nitro-2H-chromenes with mercaptoacetaldehyde: stereoselective synthesis of tetrahydro-4H-thieno[3,2-c]chromen-3-ols

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K₃PO₄–Mediated Synthesis of Chromeno–[3,4‐c]isoxazole from 3–Nitro–2H–chromene and α–Chloro Aldehyde via Michael Addition/C−Cl Bond Cleavage/Deformylation as Key Fragmentation Sequences

K₃PO₄–Mediated Synthesis of Chromeno–[3,4‐c]isoxazole from 3–Nitro–2H–chromene and α–Chloro Aldehyde via Michael Addition/C−Cl Bond Cleavage/Deformylation as Key Fragmentation Sequences