Polyphosphoric Acid-Induced Construction of Quinazolinone Skeleton from 1-(3,4-Dimethoxyphenyl)-3-phenylurea and Carboxylic Acids

Ivanov, Iliyan; Nikolova, Stoyanka; Kochovska, Ekaterina; Statkova-Abeghe, Stela

doi:10.3987/com-06-10753

Cited by 6 publications

(2 citation statements)

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“…Examples of this approach include the Michael addition of the nitrogen atom of a urea group to the C=C bond of an a,b-unsaturated carbonyl group, [194] the palladium-catalyzed intramolecular arylation of a urea group, [195] the polyphosphoric acid induced condensation of diarylureas with carboxylic acids, [196] the Brønsted acid promoted hydroamidation-hydroarylation of arylureas containing an alkyne moiety at the ortho position (to give spiroquinazolinone derivatives), [197] or the hydrazine-induced cyclization of N-arylcarbamates containing an ortho bromomethyl group. [198] 18.8.22.4…”

Section: Scheme 67 Organocatalytic Asymmetric Tetrahydropyrimidinone mentioning

confidence: 99%

Acyclic and Cyclic Ureas (Update 2013)

Banert¹,

Dobbs²,

Hall³

et al. 2013

Knowledge Updates 2013/3

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Section: Scheme 67 Organocatalytic Asymmetric Tetrahydropyrimidinone mentioning

confidence: 99%

Acyclic and Cyclic Ureas (Update 2013)

Banert¹,

Dobbs²,

Hall³

et al. 2013

Knowledge Updates 2013/3

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“…The Friedel-Crafts acylation of activated benzene rings in the presence of polyphosphoric acid is a very convenient method for the direct synthesis of aromatic ketones. This reaction is applied for direct synthesis of 1-substituted 3,4-dihydroisoquinolines [4], 1-substituted 3,4-dihydroβ-carbolines [5], quinazolinones [6], isochromanes [7], etc. Besides their use as synthetic scaffolds, ketoamides are also known for their anticonvulsant [8], antidepressant [9], and antiproliferative [10] activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of N-[1-(2-Acetyl-4,5-dimethoxyphenyl)propan-2-yl]benzamide and Its Copper(II) Complex

2023

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This paper represents a convenient method for the synthesis of N- [1-(2-acetyl-4,5-dimethoxyphenyl)propan-2-yl]benzamide and its Cu(II) complex. In silico analysis predicted spasmolytic activity for the compound. Based on the in silico calculations, the importance of the predicted ketoamide, and our previous experiments, we synthesized the ketoamide via ortho-acylation of N- [1-(3,4-dimethoxyphenyl)propan-2-yl]benzamide with acetic anhydride in polyphosphoric acid. We applied the title ketoamide in reaction with Cu(II) varying the solvents. We found that the reaction leads to the formation of a coordination compound when the ligand dissolved in DMSO reacts with a water solution of CuCl 2 in an alkaline environment in a molar ratio M : L : OH -= 1 : 2 : 2. The structures of the new compounds are discussed based on their melting points, IR, 1 H, 13 C NMR and Raman spectral data.

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