Utilization of α‐halocarbonyl compounds in the synthesis of thiazole, thiadiazole, and thiophene derivatives

Abdel‐Latif, Ehab; Bondock, Samir

doi:10.1002/hc.20206

Cited by 23 publications

(11 citation statements)

References 25 publications

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“…Malonothiodiamides have found use in Hantsch syntheses [95,96]. Thus, the reaction of N-methylmalonothiodiamide 184 with α-bromoacetophenone leads to the formation of 2-(N-methylaminocarbonyl)methyl-4-phenylthiazole 185 [95].…”

Section: [3+2] Cyclocondensation Of Malono(di)thioamides With 12-diementioning

confidence: 99%

“…The latter enters into reaction with benzylidenemalononitrile, resulting in the isolation of 2-amino-3-cyano-1-methyl-6-oxo-4-phenyl-5-(4-phenyl-1,3-thiazol-2-yl)-1,6-dihydropyridine 186. The products from the condensation of O-ethyl-N-arylmalonothioamide 187 [96] with α-halo ketones, (phenylhydrazono)bromomethyl phenyl ketone, N-aryl-2-chloroacetamide, and chloroacetyl chloride are derivatives of thiazoline 188, 1,3,4-thiadiazoline 189, thiazolidin-4-one 190, and thiophen-4-one 191 respectively.…”

Section: [3+2] Cyclocondensation Of Malono(di)thioamides With 12-diementioning

confidence: 99%

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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: [3+2] Cyclocondensation Of Malono(di)thioamides With 12-diementioning

confidence: 99%

Section: [3+2] Cyclocondensation Of Malono(di)thioamides With 12-diementioning

confidence: 99%

Heterocyclization of thioamides containing an active methylene group (review)

Britsun

Esipenko

Lozinskii

2008

Chem Heterocycl Comp

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“…[15][16][17][18][19] These compounds were found to be associated with a wide range of chemotherapeutic activities. 20 In continuation of our interest in the synthesis of heterocycles containing a thiazole moiety [21][22][23][24][25][26][27][28] , we report herein the results of our study of the reactions of an enaminonitrile 2 with several nitrogen nucleophiles. The aim of the present paper is to present an efficient synthesis of novel 2-heteroaryl-thiazoles, which have not been reported hitherto.…”

Section: Introductionmentioning

confidence: 99%

Behavior of 2-cyano-3-(dimethylamino)-N-(4-phenylthiazol-2-yl)acrylamide towards some nitrogen nucleophiles

Bondock¹,

Tarhoni²,

Fadda³

2011

Arkivoc

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The versatile, hitherto unreported 2-cyano-3-(dimethylamino)-N-(4-phenylthiazol-2-yl)-acrylamide 2 was synthesized and allowed to react with hydroxylamine, hydrazine and guanidine to afford regioselectively the isoxazole 4, pyrazole 6 and pyrimidine 8 derivatives, respectively. The reaction of 2 with thiourea and / or ethyl glycinate in a basic medium afforded the regioisomeric pyrimidinethione 9 and 3,5-dioxo-1,4-diazepine-6-carbonitrile 14. Compound 2 reacts also with 2-amino-4-phenylthiazole, 2-amino-4-methylpyridine, 2-aminotetrazole, 2-aminobenzothiazole and 2-aminobenzimidazole to give the corresponding bridgehead nitrogen heterocycles namely thiazolo

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“…In continuation of our interest in the synthesis of bioactive heterocycles containing a thiazole moiety , we report herein the results of our study of the regioselective synthesis of pyrazolo[3,4‐ d ]pyrimidines, imidazo[1,2‐ b ]pyrazoles, pyrazolo[3,4‐ d ][1–3]triazine, pyrazolo[1,5‐ c ][1,3,5]triazine and pyrazolo[1,5‐ c ][1,3,5]thiadiazine incorporating a thiazole moiety, via the reactions of the versatile, readily accessible 5‐amino‐3‐(phenylamino)‐N‐(4‐phenylthiazol‐2‐yl)‐1 H ‐pyrazole‐4‐carboxamide ( 1 ) with some chemical reagents such as DMF‐DMA, isothiocyanates, α‐chlorocarbonyls and formalin.…”

Section: Introductionmentioning

confidence: 99%