An environmentally friendly approach for the synthesis of quinazolinone sulfonamide

Balalaie, Saeed; Hekmat, Shohreh; Ramezanpour, Sorour; Röminger, Frank; Kabiri-Fard, Hasan; Vavsari, Vaezeh Fathi

doi:10.1007/s00706-017-1924-x

Cited by 6 publications

(3 citation statements)

References 59 publications

(54 reference statements)

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“…All melting points were measured without corrections. Four pyridine-2,4-dione derivatives with different N-substituted tails [CH 3 , CH 2 CH 3 , CH 2 CH 2 OH, CH 2 CH 2 CH 2 OCH(CH 3 ) 2 ] were synthesised according to a previously reported paper [22]. 4-Aminobenzoic acid methyl ester (methyl 4-aminobenzoate, analytical grade) was purchased from Shanghai Ascender Chemical Co., Ltd (China).…”

Section: Experiments Materialsmentioning

confidence: 99%

Tautomerism, crystal structure, and copper(ii) complexation of pyridonylazo dyes derived from methyl 4‐aminobenzoate

Feng

Wang

Liu

et al. 2017

Coloration Technology

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Four heterocyclic dyes, derived from methyl 4-aminobenzoate and pyridine-2,4-dione components, with different N-substituents in the latter [CH 3 , CH 2 CH 3 , CH 2 CH 2 OH, CH 2 CH 2 CH 2 OCH(CH 3 ) 2 ], were synthesised by the traditional diazotisation-coupling strategy. Furthermore, a Cu(II) dye-metal complex was prepared and characterised by X-ray single-crystal diffraction for comparison, where the configuration transformation from hydrazone to deprotonated azo forms was found before and after Cu(II) ion complexation. In addition, the azo-hydrazone transformation could be observed by acid-base titration experiments. To the best of our knowledge, this work is the first structural study of pyridone dyes based on methyl 4-aminobenzoate and the corresponding dye-metal complex.

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Section: Experiments Materialsmentioning

confidence: 99%

Tautomerism, crystal structure, and copper(ii) complexation of pyridonylazo dyes derived from methyl 4‐aminobenzoate

Feng

Wang

Liu

et al. 2017

Coloration Technology

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“…A highly convenient one-pot strategy for the consecutive synthesis of quinazolinone sulfonamides was designed by Balalaie et al from the four-component reaction of isatoic anhydride 55 , aldehydes 58 , saccharin 64 , and hydrazine hydrate 65 ( Scheme 17 ) ( Balalaie et al, 2017 ). With the aid of propyl sulfonic acid functionalized SBA-15 (SBA-Pr-SO 3 H) as a heterogeneous catalyst in solvent-free conditions, the representative products 66 have been isolated in 60–90% yields after 4 h. The avoidance of solvents, utilization of readily accessible starting materials, and easy work-up procedure, are key salient features of this protocol.…”

Section: Synthesis Of Quinazolinones From Multi-component Organocatal...mentioning

confidence: 99%

Recent advances and prospects in the organocatalytic synthesis of quinazolinones

et al. 2022

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Quinazolinone, a bicyclic compound, comprises a pyrimidine ring fused at 4´ and 8´ positions with a benzene ring and constitutes a substantial class of nitrogen-containing heterocyclic compounds on account of their frequent existence in the key fragments of many natural alkaloids and pharmaceutically active components. Consequently, tremendous efforts have been subjected to the elegant construction of these compounds and have recently received immense interest in synthetic and medicinal chemistry. The domain of synthetic organic chemistry has grown significantly over the past few decades for the construction of highly functionalized therapeutically potential complex molecular structures with the aid of small organic molecules by replacing transition-metal catalysis. The rapid access to this heterocycle by means of organocatalytic strategy has provided new alternatives from the viewpoint of synthetic and green chemistry. In this review article, we have demonstrated a clear presentation of the recent organocatalytic synthesis of quinazolinones of potential therapeutic interests and covered the literature from 2015 to date. In addition to these, a clear presentation and understanding of the mechanistic aspects, features, and limitations of the developed reaction methodologies have been highlighted.

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“…135 Four-component condensation between 3-formylchromone 1a, isatoic anhydride, hydrazine, and 2-sulfobenzimide that is used as a source of the sulfonamide moiety gave rise to (chromonyl)quinazolinones 127 (Scheme 43). 136 The reaction was performed under solvent-free conditions using propylsulfonic acid-functionalized mesoporous silica (SBA-Pr-SO 3 H) as a catalyst.…”

Section: Scheme 39mentioning

confidence: 99%

Synthesis of heterocyclic analogs of isoflavone and homoisoflavone based on 3-formylchromone

et al. 2021

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The review is focused on recent developments of chemistry of synthetic analogs of natural compounds, isofl avone and homoisofl avone. The possible synthetic strategies to access heterocyclic analogs of these compounds starting from readily available 3-formylchromone and its derivatives (3-cyanochromone, 2-amino-3-formylchromone) and products of its condensation with simplest Cand N-nucleophiles are discussed. The structural features of the reaction products that depend on the nature of the reaction medium, structure of the starting compounds, and reagent ratio are considered. Particular attention is given to the application of the modern strategies of organic synthesis, namely green chemistry approaches, click reactions, domino reactions, etc. Examples of compounds of this group most promising for clinical application due to wide and pronounced pharmacological eff ects are given.

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An environmentally friendly approach for the synthesis of quinazolinone sulfonamide

Cited by 6 publications

References 59 publications

Tautomerism, crystal structure, and copper(ii) complexation of pyridonylazo dyes derived from methyl 4‐aminobenzoate

Tautomerism, crystal structure, and copper(ii) complexation of pyridonylazo dyes derived from methyl 4‐aminobenzoate

Recent advances and prospects in the organocatalytic synthesis of quinazolinones

Synthesis of heterocyclic analogs of isoflavone and homoisoflavone based on 3-formylchromone

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