p-Toluenesulfonic Acid-Catalyzed Reaction of Phthalaldehydic Acids with Difluoroenoxysilanes: Access to 3-Difluoroalkyl Phthalides

Here we communicate a method for the synthesis of 4-(4-(piperidin-1-yl)phenyl)-2-thioxo-1,2,3,4-tetrahydro-5H-chromeno[4,3-d]pyrimidin-5-one in one step. The compound was prepared by reacting 4-hydroxy-coumarin, 4-piperidinobenzaldehye, and thiourea in a catalytic quantity of p-toluenesulfonic acid. The novelty of the compound was checked by Sci-finder. The compound was analyzed by NMR spectroscopy (1H, 13C), and mass spectrometry. The computational studies indicate that the synthesized compound possesses suitable physicochemical properties, drug-likeliness features, and good oral bioavailability.

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p-Toluene-sulfonic Acid-catalyzed One-pot, Three-component Synthesis of 4-(4-(Piperidin-1-yl)phenyl)-2-Thioxo-1,2,3,4Tetrahydro-5H-Chromeno[4,3-d]Pyrimidin-5-One

Thabet

Ubeid

Shuheil

et al. 2022

Orient. J. Chem

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Ethyl 5-Formyl-1-(pyridin-3-yl)-1H-1,2,3-triazole-4-carboxylate: Synthesis, Crystal Structure, Hirshfeld Surface Analysis, and DFT Calculation

Pokhodylo

Slyvka

Goreshnik

et al. 2022

Molbank

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For the first time, 5-formyl-1-(pyridin-3-yl)-1H-1,2,3-triazole-4-carboxylate was synthesized via a two-step scheme. The molecular structure of the compound was determined by a single-crystal X-ray diffraction analysis. The Hirshfeld surface analysis was used to study various intermolecular interactions. The crystalline structure is marked by the presence of three types of π-interactions (n→π*, lp···π, and π···π) between the -C(H)=O group and triazole rings. The compound is a versatile polyfunctional building block for construction of annulated 1,2,3-triazoles.

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Difluorinated Silyl Enol Ethers as Fluorine-Containing Building Blocks for the Synthesis of Organofluorine Compounds

Guo¹,

Yu²,

Chen³

et al. 2022

Chinese Journal of Organic Chemistry

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Organofluorine compounds have been widely applied in various fields ranging from drug discovery, clinical medicines, agrochemistry, and materials science to organic synthesis, due to their special chemical and physical properties when compared with nonfluorinated analogs. In the past decades, significant progress has been made in the development of selective fluorination and fluoroalkylation for the synthesis of structurally diverse fluorine-containing molecules. Among them, the α-fluoroalkylated carbonyl group represents an important class of scaffold components in biologically active and druglike compounds. In this context, based on the use of difluorinated silyl enol ether (DFSEE) as a unique fluoroaklylating reagent, a variety of methods for the incorporation of gem-difluoroalkylated carbonyl moiety have been achieved, including aldol, Mannich, arylation, allylation, protonation, halogenation, conjugate addition, and olefination reactions. On the other hand, DFSEEs could also merge with new types of reactions such as radical-type difluoroalkylation and cascade reaction by virtue of their incredible reactive flexibility. In addition, the O-site selective addition of DFSEEs was also reported, enabling the construction of versatile gem-difluoroalkenes. Given the importance of organofluorine compounds and the synthetic potential of these avenues, herein, we highlight the recent advances in the functionalization of gem-difluorinated silyl enol ethers, which serve as key fluorine-containing building blocks for the synthesis of organofluorine compounds.

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p-Toluenesulfonic Acid-Catalyzed Reaction of Phthalaldehydic Acids with Difluoroenoxysilanes: Access to 3-Difluoroalkyl Phthalides

Cited by 3 publications

References 5 publications

p-Toluene-sulfonic Acid-catalyzed One-pot, Three-component Synthesis of 4-(4-(Piperidin-1-yl)phenyl)-2-Thioxo-1,2,3,4Tetrahydro-5H-Chromeno[4,3-d]Pyrimidin-5-One

p-Toluene-sulfonic Acid-catalyzed One-pot, Three-component Synthesis of 4-(4-(Piperidin-1-yl)phenyl)-2-Thioxo-1,2,3,4Tetrahydro-5H-Chromeno[4,3-d]Pyrimidin-5-One

Ethyl 5-Formyl-1-(pyridin-3-yl)-1H-1,2,3-triazole-4-carboxylate: Synthesis, Crystal Structure, Hirshfeld Surface Analysis, and DFT Calculation

Difluorinated Silyl Enol Ethers as Fluorine-Containing Building Blocks for the Synthesis of Organofluorine Compounds

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