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Newer chalcone scaffolds with reactive functional groups: Process, spectral and single crystal XRD studies
Niteen Borane (1) , Amar Ghanshyam Deshmukh (2) , Nidhi Harnesh Oza (3) , Rajamouli Boddula (4) , Paresh Narayan Patel (5,*)
(1) Laboratory of Bio-Organic Chemistry, Tarsadia Institute of Chemical Science, Uka Tarsadia University, Bardoli - 394350, Gujarat, India
(2) Laboratory of Bio-Organic Chemistry, Tarsadia Institute of Chemical Science, Uka Tarsadia University, Bardoli - 394350, Gujarat, India
(3) Laboratory of Bio-Organic Chemistry, Tarsadia Institute of Chemical Science, Uka Tarsadia University, Bardoli - 394350, Gujarat, India
(4) Laboratory of Bio-Organic Chemistry, Tarsadia Institute of Chemical Science, Uka Tarsadia University, Bardoli - 394350, Gujarat, India
(5) Laboratory of Bio-Organic Chemistry, Tarsadia Institute of Chemical Science, Uka Tarsadia University, Bardoli - 394350, Gujarat, India
(*) Corresponding Author
Received: 25 Dec 2022 | Revised: 25 Mar 2023 | Accepted: 30 Mar 2023 | Published: 30 Jun 2023 | Issue Date: June 2023
Chalcones are versatile scaffolds for the synthesis of various heterocyclic systems with commercial utility. This work describes the synthesis of five novel chalcone derivatives. Syntheses were performed by a simple one-pot, straightforward Claisen-Schmidt condensation catalyzed with pyrrolidine and KOH. The chalcones were prepared by condensation of 4-formylbenzonitrile with different aromatic ketones at room temperature. The structures of all compounds have been investigated by FT-IR, NMR, and HR-MS spectroscopy. In addition, one chalcone structure was characterized by single-crystal XRD study. Crystal data for C21H15NO2 (Ch2): monoclinic, space group P21/c (no. 14), a = 6.5694(3) Å, b = 33.2697(15) Å, c = 7.4516(4) Å, β = 97.563(2)°, V = 1614.47(14) Å3, Z = 4, T = 293(2) K, μ(MoKα) = 0.083 mm-1, Dcalc = 1.289 g/cm3, 16000 reflections measured (4.898° ≤ 2Θ ≤ 49.99°), 2822 unique (Rint = 0.0249, Rsigma = 0.0196) which were used in all calculations. The final R1 was 0.0484 (I > 2σ(I)) and wR2 was 0.1257 (all data). The absorption maxima of all novel products were evaluated by UV-visible spectroscopy. These well-established structures of all newly prepared chalcone scaffolds with reactive functional groups (i.e. nitrile and 2-propenone) can be exploited as a crucial intermediate in the synthesis of new heterocyclic scaffolds with fluorescence and other applications.
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The work was financially supported by the GUJCOST, Government of India (Project No. GUJCOST/2020-21/2012).
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DOI Link: https://doi.org/10.5155/eurjchem.14.2.297-302.2405
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