Reactions of Benzoylisothiocyanate with Acetoacetanilide: Synthesis of Pyrazole, Pyridine, Pyrimidine, Pyrazolo[3,4-d]pyrimidine, Pyrazolo[4,3-d]pyrimidine and Pyrido[4,3-d]oxazine Derivatives

Mohareb, Rafat M.; Aziz, Suzan Ibrahim; Abdel‐Sayed, N. I.; El-Ablack, Fawzia Z

doi:10.1135/cccc19930947

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“…Recently, our research group was involved through a series of reactions involving the reaction of active methylene reagents with phenylisothiocyanate in dimethylformamide containing potassium hydroxide to form intermediate potassium sulphide. The latter underwent heterocyclization when reacted with α‐halocarbonyl compounds to form either thiophene or thiazole derivatives depending of the reaction conditions and the nature of reagents used [24–26] . In continuation of this program, compound 4 reacted with phenylisothiocyante ( 24 ) in dimethylformamide containing potassium hydroxide to give the intermediate potassium sulphide 25 .…”

Section: Resultsmentioning

confidence: 99%

“…The latter underwent heterocyclization when reacted with αhalocarbonyl compounds to form either thiophene or thiazole derivatives depending of the reaction conditions and the nature of reagents used. [24][25][26] In continuation of this program, compound 4 reacted with phenylisothiocyante ( 24 Compound 4 reacted with phenylisothiocyanate and elemental sulfur to give the thiazole derivative 30 (Scheme 4). The structure of compound 30 was based on analytical and spectral data (see experimental section).…”

Section: Chemistryselectmentioning

confidence: 99%

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Design, Synthesis, Molecular Docking and Biological Studies of 4H‐Benzo[d][1,3]oxazin‐4‐one Derivatives and Their Uses in Heterocyclic Synthesis

2022

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2‐(4‐Oxo‐4H‐benzo[d][1,3]oxazin‐2‐yl)acetonitrile (4) was synthesized through the reaction of anthranilic acid with ethyl cyanoacetate. The reactivity of the latter product toward chemical reagents was studied to produce coumarin, ylidene, thiophene, thieno[2,3‐b]pyridine, thiazole and pyrazole derivatives. The synthesized compounds were evaluated against three cancer cell lines namely HEPG2, HONE1 and MCF and normal cell line W138. The most active compounds 4, 6, 8 b, 12, 14, 16, 18 a, 18 b, 19, 21, 23 a, 23 b, 27 a, 27 b, 29 b, 31, 33 b, 36, 38 c and 39 b were further evaluated toward c‐Met kinase inhibitions. Overall results of inhibition toward the cancer cell lines showed that most of the tested compounds have high potent effect. The obtained results of c‐Met kinase inhibitions showed that all tested compounds gave high inhibitions. The results obtained through this work encourage us for future work using benzo[d]oxazine derivatives to produce target molecules as anticancer agents. Molecular docking of compounds 4, 6 and 16 were performed.

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Section: Resultsmentioning

confidence: 99%

Section: Chemistryselectmentioning

confidence: 99%

Design, Synthesis, Molecular Docking and Biological Studies of 4H‐Benzo[d][1,3]oxazin‐4‐one Derivatives and Their Uses in Heterocyclic Synthesis

2022

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“…Heterocyclization of the intermediate potassium salts took place through their individual reaction with any of the α‐halocarbonyl derivatives. The reaction leading to the formation of either thiophene or thiazole derivatives depended on the nature of the active methylene compound that is being used . The active methylene moiety present in compound 3 showed interesting reactivity toward the formation of potassium sulfide salts.…”

Section: Resultsmentioning

confidence: 99%

Uses of ethyl benzoylacetate for the synthesis of thiophene, thiazole, pyridine, and pyran derivatives with antitumor activities

Mohareb

Mostafa

2020

Journal of Heterocyclic Chem

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The reaction of ethyl benzoylacetate with malononitrile in an oil bath at 120°C gave the condensation product 3. The latter compound underwent a series of heterocyclization to give thiophene, thiazole, pyridine, and pyran derivatives. The structures of the synthesized products were established on the basis of analytical and spectral data. The antitumor evaluation of the newly synthesized products against the six cancer cell lines namely human gastric cancer (NUGC and HR), human colon cancer (DLD1), human liver cancer (HA22T and HEPG2), human breast cancer (MCF), nasopharyngeal carcinoma (HONE1), and normal fibroblast cells (WI38) indicated that many compounds expressed high inhibition against the six cancer cell lines. Compounds 3, 8a, 8c, 14b, 16b, 16c, 16d, 19a, 19b, 20a, 22a, 27b, and 28a were the most cytotoxic compounds among the tested compounds.

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ChemInform Abstract: Reactions of Benzoylisothiocyanate with Acetoacetanilide: Synthesis of Pyrazole, Pyridine, Pyrimidine, Pyrazolo(3,4‐d)pyrimidine, Pyrano(4,3‐ d)pyrimidine and Pyrido(4,3‐d)oxazine Derivatives.

et al. 1993

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Reactions of Benzoylisothiocyanate with Acetoacetanilide: Synthesis of Pyrazole, Pyridine, Pyrimidine, Pyrazolo[3,4-d]pyrimidine, Pyrazolo[4,3-d]pyrimidine and Pyrido[4,3-d]oxazine Derivatives

Abstract: We describe in this article the results of investigations involving the reaction of benzoyl isothiocyanate I with acetoacetanilides IIa, IIb.

Cited by 3 publications

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Design, Synthesis, Molecular Docking and Biological Studies of 4H‐Benzo[d][1,3]oxazin‐4‐one Derivatives and Their Uses in Heterocyclic Synthesis

Design, Synthesis, Molecular Docking and Biological Studies of 4H‐Benzo[d][1,3]oxazin‐4‐one Derivatives and Their Uses in Heterocyclic Synthesis

Uses of ethyl benzoylacetate for the synthesis of thiophene, thiazole, pyridine, and pyran derivatives with antitumor activities

ChemInform Abstract: Reactions of Benzoylisothiocyanate with Acetoacetanilide: Synthesis of Pyrazole, Pyridine, Pyrimidine, Pyrazolo(3,4‐d)pyrimidine, Pyrano(4,3‐ d)pyrimidine and Pyrido(4,3‐d)oxazine Derivatives.

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