Reactions with Coumarins: Synthesis of Several New Annelated Pyridine and Pyrrolylcoumarin Derivatives

Ismail, Nagwa Abdallah; Khalifa, F. A.; Din, A. A. Magd El

doi:10.3987/com-90-5609

Cited by 15 publications

(5 citation statements)

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“…Thus, the reactions of 3-acetylcoumarin (71) with amides 2a,b in the presence of bases giving rise to oxo and thioxo derivatives of benzopyrano[3,4-c]pyridine 72 have been studied. 318 Cascade heterocyclisation of amides 2b,c with sodium salts of 2-hydroxymethylidenecycloalkanones 73 was examined. It was demonstrated that these reactions proceeded regioselectively to produce fused 3-cyano-1H-pyridine-2-thiones(selenones) 74.…”

Section: Cascade Heterocyclisation Involving 13-dicarbonyl Compoundsmentioning

confidence: 99%

Multicomponent cascade heterocyclisation as a promising route to targeted synthesis of polyfunctional pyridines

Литвинов¹

2003

Russ. Chem. Rev.

127

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Section: Cascade Heterocyclisation Involving 13-dicarbonyl Compoundsmentioning

confidence: 99%

Multicomponent cascade heterocyclisation as a promising route to targeted synthesis of polyfunctional pyridines

Литвинов¹

2003

Russ. Chem. Rev.

127

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“…_______ * The process of aromatization of tricyclic derivatives of coumarin by dehydrogenation was reported in [5].…”

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confidence: 99%

“…Opening of the lactone ring of the coumarin was not observed either in the case of the reaction of 3-acetylcoumarin with cyanoacetamide and its thio analog under the conditions indicated above. The reaction products were derivatives of benzopyrano [3.4-c]pyridine analogous to compound 9 mentioned previously in [5].…”

mentioning

confidence: 99%

Conversions of Coumarins Accompanied by Intermediate Opening and Recyclization of the Lactone Ring. 2. Study of the Interaction of Malonic Acid Hydrazide and Amide Derivatives with 3-Acyl(3-cyano, 3-ethoxycarbonyl)Coumarins

Nemeryuk

Dimitrova

Анисимова³

et al. 2005

Chem Heterocycl Compd

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Ethoxycarbonylacethydrazide reacts in an analogous manner. Special features have been studied of the interaction of malonic acid amide derivatives with unsubstituted coumarin and with coumarins containing electron-withdrawing groupings in position 3 of the ring.Keywords: 3-acyl(3-cyano, 3-ethoxycarbonyl)coumarins, malonic acid hydrazide and amide derivatives, mass spectrometric study of reaction products and reaction mixtures, opening and recyclization of the coumarin lactone ring, Michael reaction.Study of the interaction of 3-acyl(ethoxycarbonyl)coumarins with malonic acid dihydrazide under the conditions of the Michael reaction has shown that this reaction occurs analogously to the conversion of 3-acyl(ethoxycarbonyl)coumarins into 3-cyanocoumarins discovered by us previously [2, 3] with the formation of coumarin-3-carboxylic acid hydrazide 2.The resulting hydrazide 2, in its turn, interacts with the initial 3-acyl(ethoxycarbonyl)coumarins with the formation of salicylidene derivatives of coumarin-3-carboxylic acid hydrazides 4. The composition of the products essentially depends on the structure of the initial coumarin. In the case of coumarins unsubstituted in the benzene ring, and also their 6-methyl (6-Br) or 8-OMe derivatives, the salicylidene derivatives of coumarin-3-carboxylic acid hydrazides 4a-d predominate among the reaction products [4]. In the case of 3-ethoxycarbonyl(acetyl)coumarins the formation of the corresponding N,N'-biscoumarinoyl-2-hydrazines 3a-c was noted. These compounds are formed in insignificant amount and were not isolated in the pure state. Their presence in the reaction mixture was established by the presence in the mass spectra of the corresponding peaks for the molecular ions.

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“…Different coumarins with functional substituents in position 3 have been successfully used in the synthesis of benzopyrano [3,4-c]pyridine derivatives [2][3][4][5][6][7][8]. Bearing in mind the available data for the antibacterial [2] and antipsychotic [9] activity and different practical use of similar compounds [10] we have developed a method for the preparation of the previously unknown ammonium [1]benzopyrano [3,4-c]pyridine thiolate (1) and have studied its methylation.…”

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confidence: 99%

Condensation of Sulfur-containing Pyridine Systems. 2. Synthesis and Methylation of Triethylammonium 1-Cyano-4,5-dioxo-3,4,5,6-tetrahydro[1]benzopyrano[3,4-c]pyridine-2-thiolate

Dotsenko

Кривоколыско

Литвинов

2005

Chem Heterocycl Compd

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Reactions with Coumarins: Synthesis of Several New Annelated Pyridine and Pyrrolylcoumarin Derivatives

Cited by 15 publications

References 0 publications

Multicomponent cascade heterocyclisation as a promising route to targeted synthesis of polyfunctional pyridines

Multicomponent cascade heterocyclisation as a promising route to targeted synthesis of polyfunctional pyridines

Conversions of Coumarins Accompanied by Intermediate Opening and Recyclization of the Lactone Ring. 2. Study of the Interaction of Malonic Acid Hydrazide and Amide Derivatives with 3-Acyl(3-cyano, 3-ethoxycarbonyl)Coumarins

Condensation of Sulfur-containing Pyridine Systems. 2. Synthesis and Methylation of Triethylammonium 1-Cyano-4,5-dioxo-3,4,5,6-tetrahydro[1]benzopyrano[3,4-c]pyridine-2-thiolate

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