Synthesis and tautomerism of aryl- and hetaryl-azo derivatives of bi- and tri-heterocycles

Shawali, Ahmad S.

doi:10.1016/j.jare.2010.07.002

Cited by 33 publications

(16 citation statements)

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“…U literaturi postoje pregledni radovi koji se odnose na disperzne azo boje, uključujući i arilazo piridonske boje [7][8][9]. U okviru ovih radova uglavnom su prikazane strukture i svojstva arilazo piridonskih boja dok se njihova sinteza ne razmatra.…”

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Synthesis of azo pyridone dyes

Mijin¹,

Ušćumlić²,

Valentić³

et al. 2011

Hem Ind

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Over 50% of all colorants which are used nowdays are azo dyes and pigments, and among them arylazo pyridone dyes (and pigments) have became of interest in last several decades due to the high molar extinction coefficient, and the medium to high light and wet fastness properties. They find application generally as disperse dyes. The importance of disperse dyes increased in the 1970s and 1980s due to the use of polyester and nylon as the main synthetic fibers. Also, disperse dyes were used rapidly since 1970 in inks for the heat-transfer printing of polyester. The main synthetic route for the preparation of azo dyes is coupling reaction between an aromatic diazo compound and a coupling component. Of all dyes manufactured, about 60% are produced by this reaction. Arylazo pyridone dyes can be prepared from pyridone moiety as a coupling component, where substituent can be on nitrogen, and diazonim salts which can be derived from different substituted anilines or other heterocyclic derivatives. In addition, arylazo dyes containing pyridone ring can be prepared from arylazo diketones or arylazo ketoesters (obtained by coupling β-diketones or β-ketoesters with diazonim salts) by condensation with cyanoacetamide. Disazo dyes can be prepared by tetrazotizing a dianiline and coupling it with a pyridone or by diazotizing aniline and coupling it with a dipyridone. Trisazo dyes can be also prepared by diazotizing of aniline and coupling it with a tripyridone or by hexazotizing a trianiline and coupling it with a pyridone. The main goal of this paper is to give a brief review on the synthesis of arylazo pyridone dyes due to the lack of such reviews. In addition, some properties of arylazo pyridone dyes as light fastness and azo-hydrazon tautomerism are disccused

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unclassified

Synthesis of azo pyridone dyes

Mijin¹,

Ušćumlić²,

Valentić³

et al. 2011

Hem Ind

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“…Their IR spectra in solid sate showed bands at 3356, 3294 (NH), 1732 (ester C═O), and 1650 (cyclic amide C═O) cm À1 . 13 C NMR of compound 9c, taken as a typical example for the series prepared, revealed three signals at 14.43, 61.02, and 164.45 for CH 3 , CH 2 , and carbon of carbonyl group, respectively (Scheme 2). To rationalize the formation of the products 9, it is suggested that the reaction of 1 with 7 starts with the formation of the substitution intermediate 8.…”

Section: Resultsmentioning

confidence: 99%

Chemoselectivity in reactions of hydrazonoyl halides with ethyl 2(3H)‐permidinylideneacetate

Shawali

Farghaly

Nawar

2015

Journal of Heterocyclic Chem

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Ethyl 2(3H)‐permidinylideneacetate 1 reacted with C‐aryl‐N‐arylmethanehydrazonoyl and C‐ethoxycarbonyl‐N‐arylmethanehydrazonoyl chlorides 2 and 7 in different ways yielding 2‐(pyrazoliden‐4‐yl) perimidines 5 and substituted pyrrolo[1,2‐a] perimidines 9, respectively. The mechanisms of the reactions studied are discussed, and the structures of the products were confirmed by spectral and elemental analyses and by alternate synthesis.

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“…In contrast to these comprehensive literature reports on the chemistry of formazans, there has been no survey of their biological activities hitherto although they have been found to possess wide spectrum of biological activities such as antiviral, antimicrobial, anti-inflammatory, antifungal, anticancer, anti HIV. Based on these findings and in continuation of our studies of the chemistry of both 3-chloro-1, 5-diarylformazans 2 [17–21] and the related hydrazonoyl halides 3 [22–35] ( Chart 1 ), it was thought necessary to present this review. Our objective is to shed light on the recent developments in biological activities of various functionalized formazans 1 ( Chart 1 ).…”

Section: Introductionmentioning

confidence: 98%

Functionalized formazans: A review on recent progress in their pharmacological activities

Shawali

Samy

2015

Journal of Advanced Research

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Synthesis and tautomerism of aryl- and hetaryl-azo derivatives of bi- and tri-heterocycles

Abstract: This review summarizes results from the literature concerning synthesis and azo-hydrazone tautomerism of arylazo-and hetarylazo-derivatives of various bi-and tri-heterocycles reported by us and other research groups from 1981 to mid 2009.

Cited by 33 publications

References 106 publications

Synthesis of azo pyridone dyes

Synthesis of azo pyridone dyes

Chemoselectivity in reactions of hydrazonoyl halides with ethyl 2(3H)‐permidinylideneacetate

Functionalized formazans: A review on recent progress in their pharmacological activities

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