A Facile Synthesis of Some New Thiazolo[3, 2]pyridines Containing Pyrazolyl Moiety and Their Antimicrobial Activity

El‐Emary, Talaat I.; Khalil, A. M.; Ali, Gameel A. M. El‐Hag; El-Adasy, Abu-Bakr A.

doi:10.1080/10426500490494778

Cited by 27 publications

(8 citation statements)

References 13 publications

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“…163 On the other hand, pyrazol-4-ylmethylene malononitrile 54 125,164 could be cyclized with acetone and ammonium acetate to give the corresponding 3-amino-6-methylpyridine-2-carbonitriles 167 125 (Scheme 70). 166 On the other hand, the reaction of 58 with 2-arylidenemalononitrile derivatives 172 afforded 6-amino-2-oxo-1,2-dihydropyridine-3,5dicarbonitriles 173 167,168 (Scheme 72). On the other hand, the reaction of equimolecular amounts of 1,3-diphenyl-1H-pyrazole-4carboxaldehyde 2, appropriate aromatic ketone 41 and malononitrile 53 in the presence of aniline afforded the corresponding pyridine-3-carbonitriles 178 155 (Scheme 75).…”

Section: Oxidation Of the Corresponding Alcoholsmentioning

confidence: 99%

“…Ismail et al 118 reported that the reaction of pyrazol-4-ylmethylene malononitrile 54 with urea or thiourea 184 afforded 4,6-diamino-5-benzylidenepyrimidin-2(5H)-ones/(thiones) 190 (Scheme 82). Under various conditions multi-component reaction of pyrazole-4-carboxaldehyde 2 with ethylacetoacetate, 120,131,[187][188][189] methylacetoacetate, 131,187 acetylacetone 120,131 or butanamides 64,190,191 64 and urea, 64,120,131,187,[189][190][191] thiourea, 64,103,120,187,188,191 El-Emary et al 166 reported that the treatment of hydrazone derivative 58 with salicylaldehyde 43 yielded chromene 235 (Scheme 107).…”

Section: Scheme 79 Synthesis Of 2-oxo(thioxo)pyrimidine Derivatives 185mentioning

confidence: 99%

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Pyrazole-carboxaldehydes as versatile precursors for different pyrazole-substituted heterocyclic systems

Elwahy¹,

Abdelhamid²,

Hawass³

et al. 2021

Arkivoc

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In the last decade, interest in pyrazole chemistry has grown considerably due to the discovery of fascinating properties demonstrated by a large number of pyrazole derivatives. They occur in a wide range of natural products, dyes, and as scaffolds in a number of drugs and associated pharmaceutical active substances. Substantial attention has been paid to the creation of hybrid molecules in which two heterocycles are bound in a single molecule to enhance their biological effectiveness and overcome drug resistance. In this regard, this review illustrated various methods for the construction of pyrazole-substituted heterocycles and their corresponding fused derivatives using pyrazole carboxaldehydes as effective precursors. The heterocyclic systems mentioned in this review are categorized according to the type of the heterocyclic systems.

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Section: Oxidation Of the Corresponding Alcoholsmentioning

confidence: 99%

Section: Scheme 79 Synthesis Of 2-oxo(thioxo)pyrimidine Derivatives 185mentioning

confidence: 99%

Pyrazole-carboxaldehydes as versatile precursors for different pyrazole-substituted heterocyclic systems

Elwahy¹,

Abdelhamid²,

Hawass³

et al. 2021

Arkivoc

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“…It is thought of interest to accommodate thiazolidin-4-one and pyridine moiety in a single molecular framework. With this in mind and in continuation of our research on synthesis of biologically active antimicrobial heterocylcles [22][23][24][25][26][27][28][29][30] we are report here synthesis of some a novel series of thiazolidinones class having pyridine moiety in addition to investigation of their antimicrobial activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Antimicrobial Evaluation of Some Hitherto Unknown 4-Oxo-Thiazoles and Thiazolo [3, 2-A] Pyridines

Shedid

Ali

2018

Al-Azhar Bulletin of Science

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2-(4-Oxothiazolidin-2-ylidene) acetonitrile and ethyl-2-(4-oxothiazolidin-2-ylidene) acetate (1a, b), were condensed with anthralaldehyde (1:1 molar ratio) and gave 4, 5-dihydro-4-oxothiazole derivatives (2a, b). Refluxing of 2-(Antharacene-9-yl-methylene) malononitrile in acetic acid with thioglycollic acid gave (3). 4-Thiazolidinones containing bis aryl methylidine moieties (4a-c) and (5a, b) were produced via condensation of either (2a) or (3) with different aromatic aldehydes (1:1 molar ratio). Heating of (2a) with α-substituted cin-namonitriles gave the expected substituted thiazolo [3, 2-a] pyridines (6a-d), (8) and (10a-c). The synthesized compounds have been screened for their antimicrobial activities against some selected species of Gram-positive (G +). Gram-negative (G-) bacteria and 3 different types of fungi. They were found to be more active against Gram positive than Gram negative bacteria.

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“…5 Morpholine derivatives have been reported to possess antimicrobial, 6 hypoglycemic, 7 antagonists of leukocyte, 8 tyrosine kinas inhibitory, 9 and inhibition of collagen-induced blood aggregation. 10 Thus, in conjunction to our interest in developing syntheses for biologically interesting thiazolo[3,2-a] pyridines, [11][12][13][14][15][16][17] we disclose a new synthesized, thiazolo [3,2-a] pyridine ,pyrazolo [3,4- . The IR spectra of the reaction products showed absorption bands at 3252, 3210, 1716 and 1710cm -1 due to NH, and two(C=O thiazolidinone) groups, respectively.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Some Novel Thiazole, Thiazolo[3,2-A]pyridine and Thiazolo[3,2-A]-1,8-Naphthyridine Derivatives Containing Morpholine Moiety

Elhagali

2010

Al-Azhar Bulletin of Science

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One pot reaction of morpholin or piperidine , ethyl cyanoactate,and thioglycollic acid afforded the novel 2-(2-morpholino-2-oxo-ethylidene)-4-thiazolidinone and 2-(2-oxo-2-(piperidin-1-yl) ethylidene) thiazolidin-4-one (1a,b).Cyclization of (1a) with chloroacetonitrile and malononitrile afforded the novel thiazolidinone derivatives (2a,b).Refluxing of (1a) with o-chlorobenzaldehyde,and chloroacetonitrile furnished (3). Compound (1a) reacted with aromatic aldehydes in refluxing ethanol affording 5arylmethylidine-4-thiazolidinone (4a,b).4-Thiazolidinone derivative (4a) was condensed with hydrazine hydrate to give (5). Thiazolo [3,2-a]pyridine and pyrano [2,3-d]thiazole derivatives (6,7) were produced through reaction of (4a,b,) with a mixture aromatic aldehyde and malononitrile. Compound (6) was reacted with ethyl isot-hiocynate and hydrazine hydrate to give the corresponding thiazolopyridine derivatives (8,9) .When compound (6) was treated with each of HCOOH, C6H5CO Cl,,and CS2 and malononitrile , the novel thiazolo [3,2-a]-1,8-naphthyridine derivatives (10-13) were obtained.

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A Facile Synthesis of Some New Thiazolo[3, 2]pyridines Containing Pyrazolyl Moiety and Their Antimicrobial Activity

Cited by 27 publications

References 13 publications

Pyrazole-carboxaldehydes as versatile precursors for different pyrazole-substituted heterocyclic systems

Pyrazole-carboxaldehydes as versatile precursors for different pyrazole-substituted heterocyclic systems

Synthesis, Characterization and Antimicrobial Evaluation of Some Hitherto Unknown 4-Oxo-Thiazoles and Thiazolo [3, 2-A] Pyridines

Synthesis and Characterization of Some Novel Thiazole, Thiazolo[3,2-A]pyridine and Thiazolo[3,2-A]-1,8-Naphthyridine Derivatives Containing Morpholine Moiety

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