Thiophenylhydrazonoacetates in heterocyclic synthesis

Mohareb, Rafat M.; Sherif, Sherif M.; Gaber, Hatem M.; Ghabrial, Sami S.; Aziz, Suzan Ibrahim

doi:10.1002/hc.10205

Cited by 23 publications

(13 citation statements)

References 17 publications

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“…The latter serves as the initial reagent for subsequent reactions, including the production of thieno [2,3-b] During the reaction of cyanothioacetamide 1 and aryl(heteryl)methylene derivatives of Meldrum's acid 48 the products 49 from Michael addition were isolated [37], and their regiospecific alkylation with α-halocarbonyl compounds gave 6-alkylthio-1,2,3,4-tetrahydropyridines 50. Such reactions include the reaction of cyanothioacetamide 1 with the azo derivative of cyanoacetic ester, leading to the formation of substituted 1,6-dihydropyridazine-6-thiones 51 [38], and the synthesis of the phenylenedipyridine-2-thione derivative 52 [39]. …”

Section: Annelation Of Heterocycles By Cyanothioacetamidementioning

confidence: 99%

Heterocyclization of thioamides containing an active methylene group (review)

Britsun

Esipenko

Lozinskii

2008

Chem Heterocycl Comp

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Data from the last six years on the heterocyclization of thioamides containing an active methylene group are analyzed and classified.At the present time there has been a considerable increase in the number of publications on the chemistry of thioamides, and this is explained by the value of the compounds as initial reagents for further transformations and particularly for the synthesis of various sulfur-and nitrogen-containing heterocycles [1][2][3][4][5][6][7][8]. The enormous practical significant of the latter is common knowledge -they have found application as drugs, pesticides, dyes, and preservatives.Thioamides with an active methylene group are attractive synthesis units for the production of heterocycles. These polyfunctional compounds can be represented by the formula R 3 -CH 2 CS-NR 1 R 2 (where R 1 , R 2 = H, Alk, Ar; R 3 is an electron-withdrawing group such as CN, AlkCO, ArCO, (AlkO) 2 PO, AlkSO 2 , ArSO 2 , NO 2 ). The presence of another reaction center (the methylene group) makes it possible to use them as N-С-С and S-C-C components for various condensations [1][2][3][4][5][6][7][8]. A special feature of such substrates is the ability to react both with dinucleophilic and with dielectrophilic and dipolar reagents. As a rule the products of these heterocyclizations contain functional groups, which makes it possible to achieve their modification or annelation. Such characteristics of thioamides with an active methylene group substantially increase their synthetic potential and extend the range of accessible heterosystems, while the use of modern physical methods of investigation (X-ray crystallographic analysis and 1D and 2D NMR spectroscopy) makes it possible to establish the structure of the obtained compounds unambiguously. The presence of biological activity in the products of these transformations also attracts investigators to this subject [5][6][7][8].The reason for the appearance of this review was the increasing need for generalization and classification of new information on the heterocyclization of such thioamides that had not been included in previous reviews [2][3][4][5] and also to define the trends in the study of these processes. Since one of the most important reports in this field is the review [1] we undertook an analysis of the literature that has appeared in the last six years.

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Section: Annelation Of Heterocycles By Cyanothioacetamidementioning

confidence: 99%

Heterocyclization of thioamides containing an active methylene group (review)

Britsun

Esipenko

Lozinskii

2008

Chem Heterocycl Comp

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“…The starting materials ethyl ␣-(3-carbamoyl-4,5,6,7-tetrahydrobenzo [b]thiophen-2-ylhydrazono)acetate derivatives 1a,b were prepared as previously described in our earlier publication [15]. The reactivity of 1a,b toward some active methylene reagents is studied.…”

Section: Resultsmentioning

confidence: 99%

“…Chemical shifts are expressed in δ ppm. Compounds 1a,b were prepared according to the literature procedure [15].…”

Section: Methodsmentioning

confidence: 99%

“…The importance of such compounds is due to their diverse pharmaceutical activities including antibacterial [8,9], antidiabetic [10], anti- HIV [11], antiviral [12,13], and analgesic [14] activities. We have recently reported on the synthesis of the title precursors thiophenylhydrazonoesters 1 [15]. Such synthetic route proved to be an easy, facile, and sole approach for the synthesis of unique derivatives of pyrazoles, isoxazoles, pyrimidines, triazines, and their analogs including the tetrahydrobenzo [b]thiophene moiety.…”

Section: Introductionmentioning

confidence: 99%

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Heterocyclic synthesis with ethyl α‐(3‐carbamoyl‐4,5,6,7‐tetrahydrobenzo[b]thiophen‐2‐ylhydrazono)acetates: An expeditious synthetic approach to polyfunctionally substituted pyran, pyridine, and pyridazine derivatives

Mohareb

Sherif

Gaber

et al. 2004

Heteroatom Chemistry

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“…The usage of many pyrazole derivatives has undoubtedly created considerable attention in developing many different synthetic procedures in pharmaceuticals, agrochemicals, dyestuff. The recent developments in the synthetic routes and the chemistry of pyrazoles have been thoroughly reviewed [1][2][3][4][5]. The condensation of β-enaminonitriles and β-ketoesters with hydrazines continues to be the most widely used method for constructing the aminopyrazoles and pyrazolones, respectively [6,7].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, antimicrobial activity and absorption studies of some novel heterocyclic dyes based on 4-hexylbenzene-1,3-diol

Patel

2012

Eur. J. Chem.

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KEYWORDSAniline derivatives were diazotized and coupled with 3-aminocrotononitrile to give the corresponding 2-arylhydrazono-3-ketiminobutyronitriles. Cyclization of these arylhydrazono derivatives with hydrazine monohydrate afforded 5-amino-4-arylazo-3-methyl-1H-pyrazoles which were subsequently diazotized and coupled with malononitrile to yield a series of pyrazolylhydrazonomalononitriles. These compounds were then reacted with hydrazine monohydrate to provide, heterocyclic dyes, which were further diazotized and coupled with 4-hexylbenzene-1,3-diol to produce novel heterocyclic tetraazo dyes which were characterized by elemental analysis and spectral methods. The antimicrobial activity and absorption characteristics of the dyes were also examined in detail.Pyrazole Solvatochromism Heterocyclic dyes Antimicrobial activity 3-Aminocrotononitrile 4-Hexylbenzene-1,3-diol

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Thiophenylhydrazonoacetates in heterocyclic synthesis

Abstract: Benzo[b]thiophen-2-yl-hydrazonoesters4 were synthesized by coupling of 2-diazo-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide (1)

Cited by 23 publications

References 17 publications

Heterocyclization of thioamides containing an active methylene group (review)

Heterocyclization of thioamides containing an active methylene group (review)

Heterocyclic synthesis with ethyl α‐(3‐carbamoyl‐4,5,6,7‐tetrahydrobenzo[b]thiophen‐2‐ylhydrazono)acetates: An expeditious synthetic approach to polyfunctionally substituted pyran, pyridine, and pyridazine derivatives

Synthesis, antimicrobial activity and absorption studies of some novel heterocyclic dyes based on 4-hexylbenzene-1,3-diol

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