Iodine mediated one-pot synthesis of 3-cyano and 3-cyano-4-methylcoumarins

Sharma, Dinesh; Makrandi, J. K.

doi:10.2298/jsc130127140s

Cited by 7 publications

(5 citation statements)

References 10 publications

(11 reference statements)

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“…[89,90] There are reports on accessing coumarin architectures from phenols and βketoesters under Pechmann condensation conditions with sulfuric acid as catalyst. [91] Lastly, the synthesis of this class of scaffolds has also been reported from ketones, [92,93] such as the reaction of hydroxy acetophenone with diethyl carbonate following Claisen condensation conditions in the presence of sodium hydride. [94] In relation to the photophysical properties of coumarinbased systems, it should be noted that the core structure is characterized by absorption and fluorescence emission restricted to the UV spectral region.…”

Section: Coumarinsmentioning

confidence: 99%

“…[ 89 , 90 ] There are reports on accessing coumarin architectures from phenols and β‐ketoesters under Pechmann condensation conditions with sulfuric acid as catalyst. [91] Lastly, the synthesis of this class of scaffolds has also been reported from ketones,[ 92 , 93 ] such as the reaction of hydroxy acetophenone with diethyl carbonate following Claisen condensation conditions in the presence of sodium hydride. [94] …”

Section: Coumarinsmentioning

confidence: 99%

See 1 more Smart Citation

Mitochondrial Targeting and Imaging with Small Organic Conjugated Fluorophores: A Review

Crawford

Dimitriadi

Bassin

et al. 2022

Chemistry A European J

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The last decade has seen an increasingly large number of studies reporting on the development of novel small organic conjugated systems for mitochondrial imaging exploiting optical signal transduction pathways. Mitochondria are known to play a critical role in a number of key biological processes, including cellular metabolism. Importantly, irregularities on their working function are nowadays understood to be intimately linked to a range of clinical conditions, highlighting the importance of targeting mitochondria for therapeutic benefits. In this work we carry out an in‐depth evaluation on the progress to date in the field to pave the way for the realization of superior alternatives to those currently existing. The manuscript is structured by commonly used chemical scaffolds and comprehensively covers key aspects factored in design strategies such as synthetic approaches as well as photophysical and biological characterization, to foster collaborative work among organic and physical chemists as well as cell biologists.

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Section: Coumarinsmentioning

confidence: 99%

Section: Coumarinsmentioning

confidence: 99%

Mitochondrial Targeting and Imaging with Small Organic Conjugated Fluorophores: A Review

Crawford

Dimitriadi

Bassin

et al. 2022

Chemistry A European J

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“…Different factors were studied to optimize the reaction conditions, Scheme 8. [35] Under microwave irradiation, Sharma et al [36] developed the reaction of 2-hydroxybenzaldehydes with malononitrile in the presence of iodine as the catalyst and DMF as the solvent to afford product final, 3-cyanocoumarins, Scheme 9.…”

Section: Synthesis Of Coumarin Derivatives From Salicylaldehydementioning

confidence: 99%

“…The reaction of salicylaldehydes and ethyl 2‐cyanoacetate in the presence of potassium phtalimide led to 3‐substituted coumarins. Different factors were studied to optimize the reaction conditions, Scheme 8 [35] …”

Section: Coumarin Synthesismentioning

confidence: 99%

Synthesis and Biological Properties of Coumarin Derivatives. A Review

et al. 2021

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Coumarin and its derivatives are widely used as scaffolds in the synthesis of new heterocyclic systems. This review focuses on current developments in the synthesis of heterocyclic coumarin compounds. Numerous approaches especially involving nanoparticle catalysts have been developed to get new bioactive coumarin derivatives endowed with pharmacological and biological activities. The present work describes the reactivity and the new strategies using various catalysts for the synthesis of coumarin and its derivatives reported in the literature and their biological properties.

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“…A series of coumarins was obtained in good to excellent yields (41-92%). Synthesis of 3-cyano-4-methylcoumarions was conducted under heating and microwave conditions by Sharma and Makrandi [95]. Reactions of 2-hydroxyacetophenones with malononitrile in presence of iodine as catalyst (Scheme 61) were performed in DMF.…”

mentioning

confidence: 99%

Recent Advances in the Synthesis of Coumarin Derivatives from Different Starting Materials

et al. 2020

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The study of coumarin dates back to 1820 when coumarin was first extracted from tonka bean by Vogel. Compounds containing coumarin backbone are a very important group of compounds due to their usage in pharmacy and medicine. Properties and biological activities of coumarin derivatives have a significant role in the development of new drugs. Therefore, many different methods and techniques are developed in order to synthesize coumarin derivatives. Coumarin derivatives could be obtained from different starting materials with various methods but with big differences in yield. This review summarized various methods, techniques and reaction conditions for synthesis of coumarins from different compounds such as aldehydes, phenols, ketones and carboxylic acids.

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Iodine mediated one-pot synthesis of 3-cyano and 3-cyano-4-methylcoumarins

Cited by 7 publications

References 10 publications

Mitochondrial Targeting and Imaging with Small Organic Conjugated Fluorophores: A Review

Mitochondrial Targeting and Imaging with Small Organic Conjugated Fluorophores: A Review

Synthesis and Biological Properties of Coumarin Derivatives. A Review

Recent Advances in the Synthesis of Coumarin Derivatives from Different Starting Materials

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