Synthesis of some new azo pyrazolo[1,5-a]pyrimidine-thieno[2,3-b]pyridine derivatives and their application as disperse dyes

Ho, Yuh-Wen

doi:10.1016/j.dyepig.2004.06.007

Cited by 83 publications

(46 citation statements)

References 10 publications

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“…We have previously reported the synthesis of novel heterocyclic systems such as 2-[[4-(arylazo)-3,5-disubstituted-pyrazol-1-yl]carbonyl]-thieno [2,3-b]pyridines [19] and 3-(2-methyl-5,7-disubstituted-pyrazolo[1,5-a]pyrimidine-3-yl)azo-4,6-disubstituted-thieno [2,3-b]pyridine derivatives [20] and their application to polyester fibers as disperse dyes, which gave encouraging results. As a continuation of our previous work, we report here the synthesis of a series of new heterocyclic monoazo dyes derived from novel diazonium components, the polyfunctionally substituted 3-amino-4-trifluoromethylthieno [2,3-b]pyridines synthesized from 3-cyano-4-trifluoromethyl-6-substituted-2(1H )-pyridinethiones and their use as disperse dyes for polyester fibers.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and properties of heterocyclic monoazo dyes derived from 3-cyano-4-trifluoromethyl-6-substituted-2(1H)-pyridinethiones

Yao

2006

Dyes and Pigments

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Section: Introductionmentioning

confidence: 99%

Synthesis and properties of heterocyclic monoazo dyes derived from 3-cyano-4-trifluoromethyl-6-substituted-2(1H)-pyridinethiones

Yao

2006

Dyes and Pigments

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“…The structure of compound 13 was assigned on the basis of elemental analysis and spectral data which agree with the proposed structure (Scheme 2). 5-Aminopyrazole 13 has been emphasized as a new synthetic auxiliary used for the preparation of pyrazolo [1,5-a]pyrimidine derivatives [14,15], which associated with a great applications in pharmaceutical fields [16][17][18][19] and dyestuff industry [20,21]. Thus, the reaction of compound 13 with acetylacetone in refluxing glacial acetic acid afforded 4-(5,7-dimethyl-2-hydroxypyrazolo [1,5- (14).…”

mentioning

confidence: 99%

Ethyl {4‐[2‐(saccharin‐2‐yl)acetylsulfamoyl]phenylazo}cyanoacetate in the synthesis of polyfunctionally heteroaromatic derivatives

Aly

2009

Journal of Heterocyclic Chem

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magnified imageAn efficient and direct one‐pot reaction of ethyl saccharinylcyanoacetate derivative 3 with a variety of active methylene reagents and nitrogen nucleophiles afforded novel series of polyfunctionally substituted heteroaromatic derivatives 5–13, respectively. The pyrazole derivative 13 was seemed to be the excellent precursors for the synthesis of pyrazolo[1,5‐a]pyrimidine derivatives 14–24. The antimicrobial screening of some synthesized products was evaluated against some selected bacteria and fungi. The structures of the synthesized derivatives were established by elemental and spectral data. J. Heterocyclic Chem., (2009).

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“…Pyrazoles are an interesting group of compounds because they have a broad spectrum pharmacologically properties such as antibacterial, 1 antihyperglycemice analgesic, 2 antiparasitic, 3 antimicrobial 4 and antischistosomal activities. 5 The pyrazole synthesis of particular use because there are themselves building block for a variety of pyrazole containing structure such as pyrazoloisoquinolines, 6 pyrazolopyrimidines, 7 pyrazolopyridines , 8 pyrazolopyrazines 9 and pyrazolotriazoles.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Fastness and Spectral Properties of Some New Azo Pyrazole and Pyrazolotriazole Derivatives

Rizk¹,

El‐Badawi²,

Ibrahim³

et al. 2010

Journal of the Korean Chemical Society

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Diazotization of sodium nitrite/ortho-phosphoric acid 조건에서 5-amino-1,3-diaryl-1H-pyrazoles 1a-c를 diazotization화 반응시 킨 다음에, aryl amines과 반응시켜서 o-aminoazo compounds 5a-f를 합성하였다. 합성한 화합물 5a-f를 pyridine/cupric acetate 반응 조건에서 반응시켜서 triazole 6a-f들을 합성하였으며, 얻어진 화합물 6a-f을 aryl diazonium salts과 반응시켜서 화합물 7a-j을 합성하였다. 합성한 염료 화합물을 polyesters에 분산염료와 정착성을 측정하였다.ABSTRACT. Coupling of 5-amino-1,3-diaryl-pyrazoles 1a-c with diazonium salts of different aryl amines gave a series of novel 1,3-diaryl-5-amino-4-arylazopyrazoles 3a-l. Such compounds could be also obtained by reaction of 5-amino-1,3-diaryl-4-nitroso-1H-pyrazoles 2a-c with different aryl amines in alkaline medium. Oxidation of azo derivatives 3a-l with cupric acetate, in dimethyl formamide and stream of air, gave 2,4,6-triaryl-2,4-dihydropyrazolo [4,3-d]-1,2,3-triazoles 4a-l. and the fluorescence properties of the cyclic triazoles were studied. Diazotization of 5-amino-1,3-diaryl-1H-pyrazoles 1a-c by sodium nitrite in ortho-phosphoric acid followed by coupling with some aryl amines gave o-aminoazo compounds 5a-f. Cyclisation of compounds 5a-f in pyridine and cupric acetate gave the corresponding triazoles 6a-f. The coupling of compounds 6a-f with different aryl diazonium salts gave compounds 7a-j. The synthesized dyes were applied to polyesters as disperse dyes and the fastness properties were evaluated.

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Synthesis of some new azo pyrazolo[1,5-a]pyrimidine-thieno[2,3-b]pyridine derivatives and their application as disperse dyes

Cited by 83 publications

References 10 publications

Synthesis and properties of heterocyclic monoazo dyes derived from 3-cyano-4-trifluoromethyl-6-substituted-2(1H)-pyridinethiones

Synthesis and properties of heterocyclic monoazo dyes derived from 3-cyano-4-trifluoromethyl-6-substituted-2(1H)-pyridinethiones

Ethyl {4‐[2‐(saccharin‐2‐yl)acetylsulfamoyl]phenylazo}cyanoacetate in the synthesis of polyfunctionally heteroaromatic derivatives

Synthesis, Fastness and Spectral Properties of Some New Azo Pyrazole and Pyrazolotriazole Derivatives

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