Reactions of 4-Chloro-3-formylcoumarin with Arylhydrazines

Strakova, I. A.; Петрова, М. В.; Belyakov, Sergey; Strakovs, A.

doi:10.1023/b:cohc.0000018338.41222.a2

Cited by 21 publications

(8 citation statements)

References 4 publications

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“…Several simple coumarin derivatives were synthesised from 7-hydroxycoumarin, and derivatives, using a plethora of interesting synthetic strategies [89,113,[191][192][193][194][195][196][197][198][199][200][201][202][203]. Nacetylglucosamides with coumarin aglycones have also been synthesised from 7-hydroxycoumarins [204].…”

Section: From Hydroxy/alkoxycoumarins and Thiocoumarinsmentioning

confidence: 99%

Simple Coumarins and Analogues in Medicinal Chemistry: Occurrence, Synthesis and Biological Activity

Borges¹,

Roleira²,

Milhazes³

et al. 2005

CMC

890

458

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Coumarins, also known as benzopyrones, are present in remarkable amounts in plants, although their presence has also been detected in microorganisms and animal sources. The structural diversity found in this family of compounds led to the division into different categories, from simple coumarins to many other kinds of policyclic coumarins, such as furocoumarins and pyranocoumarins. Simple coumarins and analogues are a large class of compounds that have attracted their interest for a long time due to their biological activities: they have shown to be useful as antitumoural, anti-HIV agents and as CNS-active compounds. Furthermore, they have been reported to have multiple biological activities (anticoagulant, anti-inflammatory), although all these properties have not been evaluated systematically. In addition, their enzyme inhibition properties, antimicrobial and antioxidant activities are other foremost topics of this field of research. The present work is to survey the information published or abstracted from 1990 till 2003, which is mainly related to the occurrence, synthesis and biological importance of simple coumarins and some analogues, such as biscoumarins and triscoumarins. Data are also highlighted, concerning the development of new synthetic strategies that could help in drug design and in the work on SAR or QSAR.

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Section: From Hydroxy/alkoxycoumarins and Thiocoumarinsmentioning

confidence: 99%

Simple Coumarins and Analogues in Medicinal Chemistry: Occurrence, Synthesis and Biological Activity

Borges¹,

Roleira²,

Milhazes³

et al. 2005

CMC

890

458

View full text Add to dashboard Cite

show abstract

“…Various methods reported for their synthesis so far employed the use of hazardous solvents like diphenylnitrilimine [18], acetic acid [19], pyridine [20], xylene [21] and harmful catalysts like hydrochloric acid [22], triethylamine [23], etc. These procedures were "greenified" for the desired organic functional group transformation by conducting the reaction in water.…”

Section: Resultsmentioning

confidence: 99%

Reaction of Coumarin Derivatives with Nucleophiles in Aqueous Medium

Kidwai

Priya

Rastogi

2008

Zeitschrift Für Naturforschung B

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A series of heterocycles was synthesized by the reaction of α, β -unsaturated ketones of benzopyrans or coumarins with various nucleophiles in aqueous medium bearing two points of diversity. Compared to an identical library generated by conventional parallel synthesis, a microwaveassisted procedure dramatically decreased reaction times from hours to minutes, and yields of products and intermediates were improved remarkably. This synthetic approach is ecofriendly in nature which features water as solvent, microwave irradiation, and usage of a "green" catalyst (K 2 CO 3 ).

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“…The preparation of chromen[4,3- c ]pyrazol-4-ones 9 from the reaction of 3-formyl-4-chlorocoumarin ( 5 ) with the appropriate aryl or alkyl hydrazine hydrochloride in the presence of base was intensively investigated ( Scheme 3 ) [ 10 , 18 , 19 , 25 , 26 , 27 , 28 , 29 , 30 ]. Compound 9a was employed as starting material to enrich the derivatives of chromen[4,3- c ]pyrazol-4-ones 10–12 through the reaction with benzyl bromides [ 26 ], alkyl sulfonyl chlorides [ 28 ], or N -piperazine sulfonyl chlorides [ 30 ] ( Scheme 4 ).…”

Section: Synthesis Of Benzopyrone-fused Five-membered Aromatic Heterocyclesmentioning

confidence: 99%

“…To overcome this problem, the reaction was carried out by increasing the iodine ratio to 10% and raising the temperature to 120 °C, which gave good results. This pathway has an advantage over the previous pyrazole construction methods which were relatively unstable and gave a mixture of isomeric 1-aryl and 2-arylpyrazolo[4,3- c ]coumarins [ 25 , 39 ].…”

Section: Synthesis Of Benzopyrone-fused Five-membered Aromatic Heterocyclesmentioning

confidence: 99%

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Synthetic Routes to Coumarin(Benzopyrone)-Fused Five-Membered Aromatic Heterocycles Built on the α-Pyrone Moiety. Part II: Five-Membered Aromatic Rings with Multi Heteroatoms

El‐Sawy

Abdelwahab²,

Kirsch

2021

Molecules

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Coumarins are natural heterocycles that widely contribute to the design of various biologically active compounds. Fusing different aromatic heterocycles with coumarin at its 3,4-position is one of the interesting approaches to generating novel molecules with various biological activities. During our continuing interest in assembling information about fused five-membered aromatic heterocycles, and after having presented mono-hetero-atomic five-membered aromatic heterocycles in Part I. The current review Part II is intended to present an overview of the different synthetic routes to coumarin (benzopyrone)-fused five-membered aromatic heterocycles with multi-heteroatoms built on the pyrone ring, covering the literature from 1945 to 2021.

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Reactions of 4-Chloro-3-formylcoumarin with Arylhydrazines

Cited by 21 publications

References 4 publications

Simple Coumarins and Analogues in Medicinal Chemistry: Occurrence, Synthesis and Biological Activity

Simple Coumarins and Analogues in Medicinal Chemistry: Occurrence, Synthesis and Biological Activity

Reaction of Coumarin Derivatives with Nucleophiles in Aqueous Medium

Synthetic Routes to Coumarin(Benzopyrone)-Fused Five-Membered Aromatic Heterocycles Built on the α-Pyrone Moiety. Part II: Five-Membered Aromatic Rings with Multi Heteroatoms

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