Metal-Free Synthesis of Biaryl- and Teraryl-Cored Diarylmethanes by Ring Transformation of 2H-Pyran-2-ones

Singh, Fateh V.; Kole, Priyanka B.

doi:10.1055/s-0037-1610332

Cited by 14 publications

(8 citation statements)

References 12 publications

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“…In our earlier research studies, 2H-pyran-2-ones have been proved as versatile substrates to achieve the synthesis of various scaffolds such as m-teraryls, [43] polycyclic compounds, [44,45] and pyridines [46,47] and diarylmethanes. [48] 2Hpyran-2-ones can react with nucleophiles as they are having three electrophilic centres C-2, C-4, C-6. The nucleophilic species attacks at C-6 position due to extended conjugation and presence of cyano group at position 3 of the pyran ring.…”

Section: Resultsmentioning

confidence: 99%

Metal‐Free Synthesis of Thermally Stable Fluorescent p‐Terphenyls by Ring Transformation of 2H‐Pyran‐2‐ones

Chandrasekar

Singh

2020

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A metal-free approach for the synthesis of p-terphenyls 7 a-i and cyclic p-terphenyls 9 ad and 11 ad is described via carbanion induced ring transformation reaction of 6-biphenyl-2H-pyran-2-ones 5 with malononitrile 6, cyclohexanone 8 and 1,4-cyclohexanedione monoethylene ketal 10 respectively. Additionally, the base-mediated ring transformation reactions were working smoothly under mild reaction conditions and ring transformation products 7, 9 and 11 were isolated in good to excellent yields. The synthetic approach provides the flexibility of introducing of both electron-withdrawing and-donating functionalities in p-terphenyl architecture. Moreover, the photo physical properties of compounds 7, 9 and 11 were analyzed using UV-visible and Fluorescence Spectroscopy. p-Terphenyls 7 c showed cyan fluorescence in chloroform (λ max (em): 508 nm) and acetonitrile (λ max (em): 420 nm) while cyclic p-terphenyl 9 a showed blue fluorescence in chloroform and 1,4-dioxane (λ max (em): 470 nm). Similarly, compound 11 a showed blue fluorescence in chloroform (λ max (em): 468 nm) and 1,4-dioxane (λ max (em): 473 nm). Additionally, the thermal stability of synthesized cyclic p-terphenyls 11 a, 11 c and 11 d were also studied using TG and DTA techniques.

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Section: Resultsmentioning

confidence: 99%

Metal‐Free Synthesis of Thermally Stable Fluorescent p‐Terphenyls by Ring Transformation of 2H‐Pyran‐2‐ones

Chandrasekar

Singh

2020

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“…33,34 Recently, Singh and Kole developed a metal-free approach for the synthesis of functionalized diarylmethanes by the ring transformation of 2H-pyran-2-ones with 1,3-diphenylacetone under mild reaction conditions. 35 The synthesis of highly functionalized diarylmethanes 7 was achieved in three chemical steps starting from ethyl-2-cyano-3,3-bis(methylthio)acrylate-2H-pyran-2-ones 1 (Scheme 1). 35,36 The details of all the synthesized diarylmethanes 7a-j is summarized in Table 1.…”

Section: Introductionmentioning

confidence: 99%

“…35 The synthesis of highly functionalized diarylmethanes 7 was achieved in three chemical steps starting from ethyl-2-cyano-3,3-bis(methylthio)acrylate-2H-pyran-2-ones 1 (Scheme 1). 35,36 The details of all the synthesized diarylmethanes 7a-j is summarized in Table 1.…”

Section: Introductionmentioning

confidence: 99%

Structural, Electronic, Vibrational and Pharmacological Investigations of Highly Functionalized Diarylmethane Molecules Using DFT Calculations, Molecular Dynamics and Molecular Docking

Kole

Kollur

Revanasiddappa

et al. 2022

Polycyclic Aromatic Compounds

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Present work describes the UV-Visible and FT-IR spectral behavior of highly functionalized diarylmethanes via theoretical investigations. Analyses of both theoretical and experimental UV data were in good agreement with the assigned bands. In addition, calculations pertaining to natural bond orbitals (NBOs) and mapped molecular electrostatic potential surface (MEPS) were also performed, revealing that the strongest hyperconjugative intramolecular interactions involves the p ⟶ p * , LP ⟶ r * and n ! p Ã transitions in the D and A rings. Further, the theoretical vibrational analysis revealed several characteristic vibrations that may be used as a diagnostic tool for other diarylmethanes and also indicated that the experimental bands related to the nitrile group occur in regions lower than usual, which confirms high conjugation of the triple bond with the aromatic system. Molecular dynamics (MD) and molecular docking calculations were performed in order to evaluate the behavior of such molecules in aqueous medium and the pharmacological potential. Another interesting observation in this study is the HOMO-LUMO analysis, which showed that the global reactivity values changed according to the type of substituent groups.

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“…The fascinating chemistry of 2H-pyran-2-ones has sparked much attention over the past several decades since they serve as excellent starting materials for the synthesis of a wide range of molecular structures. Recently, we have demonstrated the synthesis of 2-tetralones 20 , diarylmethanes 21 , m-terphenyls 22 , tetrahydroisoquinolines 23 , allylbenzenes 24 and prenylarenes 25 .…”

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confidence: 99%

Ultrasound-Assisted Rapid Synthesis of Functionalized 1,2-Teraryls by Ring Transformation Methodology

Krishnan

Singh

2022

Synthesis

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The function of styryl acetate as a carbanion nucleophile source has been explored in the ring transformation reaction of 2H-pyranones. The ultrasound assisted carbanion induced ring transformation of 4-amino-6-aryl-3-cyano-2H-pyran-2-ones using (E)-styryl acetate in the presence of KOH and DMF at room temperature is presented as an alternative strategy for the synthesis of functionalized 1,2-teraryls in high yields. This metal-free methodology provides easy access to a series of 1,2-teraryls and features broad functional group tolerance and mild reaction condition. Single crystal X-ray diffraction analysis of 4-(piperidin-1-yl)-6-(thiophen-2-yl)-[1,1'-biphenyl]-3-carbonitrile indicated that the crystal belongs to monoclinic system with a P21 space group having twisted aryl rings.

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Metal-Free Synthesis of Biaryl- and Teraryl-Cored Diarylmethanes by Ring Transformation of 2H-Pyran-2-ones

Cited by 14 publications

References 12 publications

Metal‐Free Synthesis of Thermally Stable Fluorescent p‐Terphenyls by Ring Transformation of 2H‐Pyran‐2‐ones

Metal‐Free Synthesis of Thermally Stable Fluorescent p‐Terphenyls by Ring Transformation of 2H‐Pyran‐2‐ones

Structural, Electronic, Vibrational and Pharmacological Investigations of Highly Functionalized Diarylmethane Molecules Using DFT Calculations, Molecular Dynamics and Molecular Docking

Ultrasound-Assisted Rapid Synthesis of Functionalized 1,2-Teraryls by Ring Transformation Methodology

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