A greener approach towards the synthesis of N-heterocyclic thiones and selones using the mechanochemical technique

Kumar, Siddharth Sanjay; Rangarajan, Shalini; Kunchur, Harish S.; Balakrishna, Maravanji S.

doi:10.1039/d2dt02322a

Dalton Trans.

2022

DOI: 10.1039/d2dt02322a

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A greener approach towards the synthesis of N-heterocyclic thiones and selones using the mechanochemical technique

Siddharth Sanjay Kumar

Shalini Rangarajan

Harish S. Kunchur

et al.

Abstract: This manuscript describes the synthesis of N-heterocyclic thiones and selones of a variety of imidazolium salts involving an eco-friendly and solventless ball-milling technique. The products have been isolated in almost...

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Cited by 4 publications

References 80 publications

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Independent LUMO Reactivity in Mesoionic N‐Heterocyclic Thiones: Synthesis of a Stable Radical Anion

Maji,

Gope,

Sharma

et al. 2024

Angewandte Chemie

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Mesoionic compounds, with positive and negative charges, are expected to have dual‐site highest occupied molecular orbital (HOMO, donor) and lowest unoccupied molecular orbital (LUMO, acceptor) reactivity. Herein, we report a novel class of air‐stable mesoionic N‐heterocyclic thiones (mNHTs) synthesized from abnormal N‐heterocyclic carbenes (aNHCs). DFT studies revealed a highly polarized exocyclic thione moiety and computed Fukui function analysis suggests the dual‐site HOMO/LUMO reactivity of mNHTs predicting donor property at the negatively charged ‘S’ center while acceptor property at the cationic imidazole ring. The independent LUMO reactivity of the mNHT was realized by its chemical reduction to an elusive radical anion, which was characterized by a single crystal X‐diffraction study. Further, we explore the reactivity of radical anion for the activation of SO2 gas, C‐Br bonds of aryl bromide and photocatalytic functionalization of C‐X (X = F, Br) bonds. This work unlocks the independent LUMO reactivity of a mesoionic compound.

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Independent LUMO Reactivity in Mesoionic N‐Heterocyclic Thiones: Synthesis of a Stable Radical Anion

Maji,

Gope,

Sharma

et al. 2024

Angewandte Chemie

View full text Add to dashboard Cite

show abstract

Independent LUMO Reactivity in Mesoionic N‐Heterocyclic Thiones: Synthesis of a Stable Radical Anion

Maji,

Gope,

Sharma

et al. 2024

Angew Chem Int Ed

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Reaction under Ball-Milling: Solvent- and Metal-Free One-Pot Diastereoselective Synthesis of Tetrahydroquinoline Derivatives as Potential Antibacterial and Anticancer Agents

Adak,

Roy,

Saha

et al. 2024

Synlett

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A mild and efficient one-pot, three-component ball-mill assisted reaction of aldehydes, anilines, and dihydrofuran (or dihydropyran and cyclohexenone) has been described for the first time in the presence of the catalytic amount of aqueous perchloric acid (8 mol%) at room temperature under organic solvent- and metal-free condition. The reactions are fast (1 hour), providing the products with excellent yields and high diastereoselectivity. This procedure endows a simple, efficient, and cost-effective method for the diastereoselective synthesis of furano- and pyrano-tetrahydroquinolines and phenanthridinone derivatives, which are important biological compounds. The diastereomers with cis-configuration was isolated as major products. The H-H COSY, NOESY experiments and X-ray crystallographic analysis of selected compounds were performed to confirm the cis-isomer. The synthesized tetrahydroquinolines (4d and 4n) have been evaluated in-vitro for their antibacterial and anticancer activities, and it was found that both the prepared compounds showed significant antibacterial and anticancer properties.

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A greener approach towards the synthesis of N-heterocyclic thiones and selones using the mechanochemical technique

Abstract: This manuscript describes the synthesis of N-heterocyclic thiones and selones of a variety of imidazolium salts involving an eco-friendly and solventless ball-milling technique. The products have been isolated in almost...

Cited by 4 publications

References 80 publications

Independent LUMO Reactivity in Mesoionic N‐Heterocyclic Thiones: Synthesis of a Stable Radical Anion

Independent LUMO Reactivity in Mesoionic N‐Heterocyclic Thiones: Synthesis of a Stable Radical Anion

Independent LUMO Reactivity in Mesoionic N‐Heterocyclic Thiones: Synthesis of a Stable Radical Anion

Reaction under Ball-Milling: Solvent- and Metal-Free One-Pot Diastereoselective Synthesis of Tetrahydroquinoline Derivatives as Potential Antibacterial and Anticancer Agents

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