Cyanoacetic acid hydrazide in heterocyclic synthesis: A new route for the synthesis of several annelated pyran derivatives

Eldin, Sanaa M.; El‐Din, Asmaa A. Magd; Basyouni, Wahid M.

doi:10.1007/bf02977523

Cited by 6 publications

(8 citation statements)

References 4 publications

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“…Analogously, 366b (X = CO 2 Et) reacted with 365 to give 84−86% of the pyrano[2,3-d]thiazoles 368 (Scheme 108). 243 A yield of 78% of 3-Methyl-6-oxo-4-phenyl-1,6-dihydropyran-[2,3-c]pyrazole-5-carbonitrile 369 was prepared via cyclocondensation of 2 with 4-benzylidene-3-methyl-2-pyrazolin-5one (Scheme 109). 243 3.4.2.…”

Section: Synthesis Of Five-membered Rings With Two Heteroatomsmentioning

confidence: 99%

“…243 A yield of 78% of 3-Methyl-6-oxo-4-phenyl-1,6-dihydropyran-[2,3-c]pyrazole-5-carbonitrile 369 was prepared via cyclocondensation of 2 with 4-benzylidene-3-methyl-2-pyrazolin-5one (Scheme 109). 243 3.4.2. Pyridine and Their Fused Derivatives.…”

Section: Synthesis Of Five-membered Rings With Two Heteroatomsmentioning

confidence: 99%

“…Pyrano[2,3- d ]-thiazole derivatives 367 was obtained in 86–91% yields from addition of two molecules of 2-cyanomethyl-2-thiazolin-4-one 366a (X = CN) to one molecule of each of the benzylidene derivatives of cyanoacetic acid hydrazide 365 with loss of one molecule of hydrazine. Analogously, 366b (X = CO 2 Et) reacted with 365 to give 84–86% of the pyrano[2,3- d ]-thiazoles 368 (Scheme ) …”

Section: Reactions Of Acid Hydrazidesmentioning

confidence: 99%

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Acid Hydrazides, Potent Reagents for Synthesis of Oxygen-, Nitrogen-, and/or Sulfur-Containing Heterocyclic Rings

et al. 2014

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Section: Synthesis Of Five-membered Rings With Two Heteroatomsmentioning

confidence: 99%

Section: Synthesis Of Five-membered Rings With Two Heteroatomsmentioning

confidence: 99%

Section: Reactions Of Acid Hydrazidesmentioning

confidence: 99%

See 1 more Smart Citation

Acid Hydrazides, Potent Reagents for Synthesis of Oxygen-, Nitrogen-, and/or Sulfur-Containing Heterocyclic Rings

et al. 2014

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“…[43] Cyanoacetamide and their derivatives are very reactive compounds, and they are widely used as reactants or reaction intermediates, interacting with diverse reagents to create a wide range of heterocyclic compounds. [44][45][46][47][48][49][50][51] Because of the presence of carbonyl and cyano groups, their electrophilic characteristics allow them to react with raw reagents to afford azoles, [52][53][54][55] chromenes and coumarins [52,53] and make them precursors in polycondensed heterocyclic system, such as pyarazolo[1,5-a]pyrimidines, benzo[h]chromenes, pyrano[3,2g]chromenes, pyrazolo [3,4-b]pyrazines and thiazolo [3,2a]pyridines. [47,49] The importance of this chemical category was due to its valuable biological activity [56] such as pharmaceutical activities including antimicrobial, [57] antifungal, antibacterial, [58] anti-inflammatory, [59] antitumor, [60] carbonic anhydrase inhibitory [61] and anticancer properties.…”

Section: Chemistryselectmentioning

confidence: 99%

Design, Synthesis of New Pyrazoles and Chromenes as ERK‐2 Inhibitors, Apoptosis inducers and Cell cycle interrupters Based on Thiophene‐Chalcone Scaffold

Metwally

Eldaly

2022

ChemistrySelect

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Arylmethylene derivatives, chromenes and aminothiophenes were synthesized from 2-cyano-N-(4-(3-(thiophen-2yl)acryloyl)phenyl)acetamide 2. The anticancer activity of most synthetic compounds was assessed in breast cancer (MCF-7), hepatocellular carcinoma (HepG-2) and cervical cancer (HeLa), with five of arylmethylene and chromene derivatives showing highest cytotoxic activity. Further, treatment of breast cancer (MCF-7) cell lines with 4 d and 6 b, the most cytotoxic compounds; revealed down regulation for ERK-2 protein with expression concentration; 527.7 � 6.61 and 427.7 � 8.39 pg/ml, respectively compared to staurosporine; 440.9 � 5.02 pg/ml. Moreover, cell death induction was assessed by Annexin V-FITC/PI assay and these compounds caused cell death by apoptosis, besides the DNA fragmentation was assessed by gel electrophoresis and ELISA and the data showed increase in the percentage of fragmentation in treated MCF-7 of values; 30.49 % and 28.19 % in 4 d and 6 b, respectively confirming the same effect as staurosporine. The DNA-flow cytometric cell cycle analysis showed that 4 d and 4 g arrested the cell cycle at S phase and 8 b arrested it at G1/S phase. Molecular docking was carried out together with physicochemical properties prediction using DruLiTo program.

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“…Acid hydrazides are widely used as preservatives and as reagents for determining certain flavonoids and also for the production of pharmaceuticals and polymers . Indeed, acid hydrazides are efficient and common precursors in the production of various heterocycles that have enormous potential as antimicrobials, anticancer agents, pharmaceuticals, anticonvulsant, antidepressant, and anti‐inflammatory agents . In addition, these heterocycles act as herbicides and dyes .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of novel heterocycles using 1,2,3‐triazole‐4‐carbohydrazides as precursors

Mohamed

Khidre

Kariuki

et al. 2019

Journal of Heterocyclic Chem

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Herein, we report the synthesis of various heterocyclic ring systems containing 1,2,3‐triazole from the reactions of acid hydrazides and commercially available reagents, using efficient and simple procedures. Reactions of certain 1,2,3‐triazole‐4‐carbohydrazides and α‐bromoketones in boiling ethanol afforded the corresponding hydrazones rather than the expected triazines. The hydrazones could also be synthesized in 85‐90% yield via an alternative pathway that involved the reaction of 1,2,3‐triazole‐4‐carbohydrazides and 4‐acetyl‐1,2,3‐triazoles in boiling ethanol containing glacial acetic acid. Reaction of one of the 4‐carbohydrazides with carbon disulfide, followed by the reaction with hydrazine hydrate, gave 4H‐1,2,4‐triazole‐3‐thiol in 73% yield, which further reacted with other α‐bromoketones in boiling ethanol to afford 7H‐[1,2,4]triazolo[3,4‐b][1,3,4]thiadiazines in 82‐84% yields. Additionally, reactions of certain carbohydrazides with ethyl 2‐cyano‐3,3‐bis(methylthio)acrylate gave 1‐aryl‐1H‐1,2,3‐triazole‐4‐carbohydrazides rather than the expected 1H‐pyrazole‐4‐carboxylates.

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Cyanoacetic acid hydrazide in heterocyclic synthesis: A new route for the synthesis of several annelated pyran derivatives

Cited by 6 publications

References 4 publications

Acid Hydrazides, Potent Reagents for Synthesis of Oxygen-, Nitrogen-, and/or Sulfur-Containing Heterocyclic Rings

Acid Hydrazides, Potent Reagents for Synthesis of Oxygen-, Nitrogen-, and/or Sulfur-Containing Heterocyclic Rings

Design, Synthesis of New Pyrazoles and Chromenes as ERK‐2 Inhibitors, Apoptosis inducers and Cell cycle interrupters Based on Thiophene‐Chalcone Scaffold

Synthesis of novel heterocycles using 1,2,3‐triazole‐4‐carbohydrazides as precursors

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