An Efficient Method for the Synthesis of Isoxazolines Under Microwave Irradiation and Solvent-Free Conditions

Indolylvinyl ketones are valuable building blocks that can be utilized for the synthesis of numerous natural products and bioactive molecules containing an indole core motif. Herein, we describe their application for the total synthesis of some alkaloids, their analogues, and a variety of other important compounds, with an emphasis on biologically active examples.1 Introduction2 Functionalization of the Enone C=C Bond2.1 Reduction2.2 Michael Addition2.3 Cycloaddition3 Transformation of the Carbonyl Group3.1 Reduction3.2 Knoevenagel Reaction3.3 Addition of Organometallic Compounds3.4 Olefination4 Reactions Involving the Enone Conjugate System С=С–С=О4.1 Reactions with 1,2-Dinucleophiles4.2 Reactions with Compounds Bearing an Active Methylene Group4.3 Reactions with 1,3-Dinucleophiles4.4 Reactions with 1,4-Dinucleophiles5 Functionalization of the Enone Methylene Group C(O)–CH2R5.1 Acylation/Crotonic Condensation and Related Transformations5.2 Enolization6 Functionalization of the Indole Core6.1 [4+2] Cycloaddition6.2 [3+3] Annulation6.3 Electrocyclic Reactions7 Miscellaneous8 Conclusions

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“…80b Notably, this cyclization proceeded under microwave and solvent-free conditions in moderate to high yields. 81…”

Section: Scheme 67mentioning

confidence: 99%

Indolylvinyl Ketones: Building Blocks for the Synthesis of Natural Products and Bioactive Compounds

et al. 2019

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“…The heterocyclic compounds undergo the most common synthesis methods such as cyclocondensation [7] and Michal addition [8] when react with hydrazine hydrate to form a pyrazole moiety. The pyrazole moiety is a versatile lead molecule in the pharmaceutical development because of its wide range of biological activities such as antifungal [9,10], antimicrobial [11][12][13], antiviral [14], anticancer [15], antitubercular [16,17], antitumor [18], antidepressant [19] and antibacterial [20].…”

Section: Introductionmentioning

confidence: 99%

Molecular Docking Study of Novel Synthesized Pyrazole Derivatives and their Antibacterial Activity

Khumar¹,

Ezhilarasi²,

Prabha³

2018

Asian J. Chem.

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The current novel series of 1-[5-(furan-2-yl)-4,5-dihydro-3-(4-morpholinophenyl)pyrazol-1-yl]ethanone are synthesized from the 3-(furan-2-yl)-1-(4-morpholinophenyl)prop-2-ene-1-one by cyclization reaction. The 3-(furan-2-yl)-1-(4-morpholinophenyl)prop-2-ene-1-one chalcones are derived from the reaction of 4-morpholino acetophenone with substituted furfuraldehyde by common Claisen-Schmidt condensation reaction. The structures of the synthesized compounds skeleton are elucidated by IR, 1 H NMR and 13 C NMR. The antimicrobial susceptibility tests of synthesized compounds are screened against Staphylococcus aureus and Escherichia coli. From the three synthesized compounds the electron-withdrawing substitution (Br) shows good effect against the Gram-positive bacteria and the electron donating substitution (CH3) shows excellent inhibition zone against the Gram-negative bacteria at the concentration level (10 µg/mL). The molecular docking is an effective and component tool for in silico screening of bioactive compounds and Auto Dock 4.2.1 is used to find the binding interaction of synthesized compounds towards 3 selected bacterial proteins (2X5O, 3TYE, 3UDI).

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Synthesis of Benzalacetophenone-based Isoxazoline and Isoxazole Derivatives

Farooq

Ngaini

2022

COC

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The demand for natural product based drugs with less cost and efficient procedures has become a challenge to researchers. Benzalacetophenone is a natural product based species that is modified into numerous heterocyclic compounds including isoxazoline and isoxazole derivatives. The utility of isoxazoline and oxazole derivatives has been increased for the synthesis of the new and effective chemical entities to serve medicinal chemistry in the past few years. Isoxazoline and isoxazole are fascinating classes of heterocyclic compounds, which belong to N- and O-heterocycles, and are widely used as precursors for the development of drugs. This review highlights the recent work for the synthesis of mono and bis isoxazoline and isoxazole derivatives using stable benzalacetophenone and functionalization of isoxazoline and isoxazole, along with the prevailing biological properties.

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An Efficient Method for the Synthesis of Isoxazolines Under Microwave Irradiation and Solvent-Free Conditions

Cited by 4 publications

References 17 publications

Indolylvinyl Ketones: Building Blocks for the Synthesis of Natural Products and Bioactive Compounds

Indolylvinyl Ketones: Building Blocks for the Synthesis of Natural Products and Bioactive Compounds

Molecular Docking Study of Novel Synthesized Pyrazole Derivatives and their Antibacterial Activity

Synthesis of Benzalacetophenone-based Isoxazoline and Isoxazole Derivatives

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