Novel synthesis of thieno[2,3‐<i>b</i>]pyridine and substituted 2‐thienylthiourea derivatives as antibiotic agents

Al‐Omran, Fatima; El‐Khair, Adel A.

doi:10.1002/jhet.5570410610

Cited by 32 publications

(14 citation statements)

References 17 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…As a result of the transformations triethylammonium 1-cyano-4,5-dioxo-3,4,5,6-tetrahydro[1]benzopyrano [3,4-c]pyridine-2-thiolates 37 [34], 6,7-dihydrothieno[2,3-b]pyridines 38 [33] and 39 [32], and 4-aryl-3-cyano-5,6-dihydro-1-benzothiepino [5,4-b]pyridine-2(1H)-thiones 40 [35] Recyclization as a Method for the Synthesis of Derivatives of 3-cyanopyridine-2-thione. The cycloacylation of cyanothioacetamide 1 with diketene can be regarded formally as recyclization.…”

Section: Annelation Of Heterocycles By Cyanothioacetamidementioning

confidence: 99%

“…Cyanothioacetamide has found use for the annelation of heterocycles, which can be regarded as a method for "making up" the 3-cyano-2-thioxopyridine ring to structures containing vicinal amino and cyano groups [32,33], or an activated double bond [34,35]. As a result of the transformations triethylammonium 1-cyano-4,5-dioxo-3,4,5,6-tetrahydro[1]benzopyrano [3,4-c]pyridine-2-thiolates 37 [34], 6,7-dihydrothieno[2,3-b]pyridines 38 [33] and 39 [32], and 4-aryl-3-cyano-5,6-dihydro-1-benzothiepino [5,4-b]pyridine-2(1H)-thiones 40 [35] Recyclization as a Method for the Synthesis of Derivatives of 3-cyanopyridine-2-thione.…”

Section: Annelation Of Heterocycles By Cyanothioacetamidementioning

confidence: 99%

See 1 more Smart Citation

Heterocyclization of thioamides containing an active methylene group (review)

Britsun

Esipenko

Lozinskii

2008

Chem Heterocycl Comp

View full text Add to dashboard Cite

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.

show abstract

Section: Annelation Of Heterocycles By Cyanothioacetamidementioning

confidence: 99%

Section: Annelation Of Heterocycles By Cyanothioacetamidementioning

confidence: 99%

Heterocyclization of thioamides containing an active methylene group (review)

Britsun

Esipenko

Lozinskii

2008

Chem Heterocycl Comp

View full text Add to dashboard Cite

show abstract

“…Furthermore, refluxing of equimolar amounts of compounds 2 and cyanothioacetamide in ethanol containing a catalytic amount of piperidine [40] afforded pyridothienopyridine-3-carbonitrile derivative 11 which its 1 H NMR spectrum showed two deuterium oxide exchangeable singlets at d 4.50 and 6.90 ppm attributed to NH 2 and NH protons; respectively. When o-aminonitrile derivative 2 was treated with benzofuran-2(3H)-one in dioxane containing a catalylic amount of triethylamine, it furnished a single product identified as compound 12.…”

Section: Chemistrymentioning

confidence: 99%

Utility of thieno[2,3-b] pyridine derivatives in the synthesis of some condensed heterocyclic compounds with expected biological activity

Hassan¹,

Sarg²,

Said³

et al. 2013

Univers Org Chem

View full text Add to dashboard Cite

“…MS were measured on a HP5988A spectrometer (Hewlett-Packard Company, Palo Alto, California). 1 H NMR spectra were recorded in CDCl 3 on a Varian Mercury Plus 400 (400 Hz) spectrometer (Varian Company, Palo Alto, California), and chemical shifts (δ) are given in ppm using (CH 3 ) 4 Si as an internal reference (δ = 0). Elementary analyses were taken on a Perkin-Elmer CHN2400 elemental analysis instrument (PerkinElmer Company, Waltham, Massachusetts).…”

Section: Methodsmentioning

confidence: 99%