Application of ortho-acylated phenylacetic acid esters to the synthesis of 1-substituted isochromanes

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

doi:10.3998/ark.5550190.0008.f05

Cited by 8 publications

(1 citation statement)

References 27 publications

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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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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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Synthesis of Oxacycles Employing the Oxa‐Pictet–Spengler Reaction: Recent Developments and New Prospects

2011

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The oxa‐Pictet–Spengler cyclization is the oxygen variation of the Pictet–Spengler reaction, in which an aromatic alcohol component (generally a β‐arylethyl alcohol) reacts with acarbonyl component (aldehyde, ketone or their masked derivatives), to yield a 1‐substituted (or 1,1′‐disubstituted)pyran fused to the aromatic ring system found in the starting alcohol. The transformation is usually promoted by Brønsted and Lewis acids. Intramolecular versions of the reaction are also known, where both components are mutually masked as an acetal. Discussed here are aspects concerning the most recent developments and new applications of this useful reaction, including the scope and limitations of new promoters, and new mechanistic pictures of this transformation. The use of novel stereochemical control strategies and the application of the reaction to the synthesis of natural products and their analogs, as well as to accessing fully synthetic bioactive compounds and new ring systems are presented, and chiral versions of the oxa‐Pictet–Spengler are also analyzed.

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Synthesis of isochromans via Fe(OTf)2-catalyzed Oxa-Pictet–Spengler cyclization

et al. 2018

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Application of ortho-acylated phenylacetic acid esters to the synthesis of 1-substituted isochromanes

Cited by 8 publications

References 27 publications

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

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

Synthesis of Oxacycles Employing the Oxa‐Pictet–Spengler Reaction: Recent Developments and New Prospects

Synthesis of isochromans via Fe(OTf)2-catalyzed Oxa-Pictet–Spengler cyclization

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