An efficient one-pot synthesis of spirooxindole derivatives by three-component reaction of isatins, malononitrile (cyanoacetic ester) and 1,3-dicarbonyl compounds in water in the presence of l-proline is reported This new protocol has the advantages of environmental friendliness, higher yields, shorter reaction times, low cost, and convenient operation

Efficient one-pot synthesis of spirooxindole derivatives catalyzed by L-proline in aqueous medium.

A simple and clean procedure for three-component synthesis of spirooxindoles in aqueous medium

Laboratory control of antimicrobial therapy

Thiazole-containing compounds as therapeutic targets for cancer therapy.

An efficient one-pot synthesis of spiro[indoline-3,4′-pyrano[2,3-c]pyrazole] derivatives by four-component reaction of hydrazine, β-keto ester, isatin, and malononitrile or ethyl cyanoacetate catalyzed by piperidine under ultrasound irradiation is described. This synthesis was confirmed to follow the group-assistant-purification chemistry (GAP) chemistry process, which can avoid traditional chromatography and recrystallization purifications.

Rapid and efficient ultrasound-assisted method for the combinatorial synthesis of spiro[indoline-3,4'-pyrano[2,3-c]pyrazole] derivatives.

Synthesis and evaluation of some new spiro indoline-based heterocycles as potentially active antimicrobial agents.

Benzo[1,2-b:5,4-b′]difuran-2-carbohydrazides 5a, b were reacted with aryl or alkyl isothiocyanates to give the corresponding thiosemicarbazides 6a–h. Cyclization of the substituted thiosemicarbazides with sodium hydroxide led to the formation of benzo[1,2-b:5,4-b′]difuranyl-1,3,4-triazoles 7a–f. Desulfurization of thiosemicarbazides by mercuric oxide gave benzo[1,2-b:5,4-b′]difuranyl-1,3,4-oxadiazoles 8a–f. Treatment of thiosemicarbazides with ethyl bromoacetate or α-bromopropionic acid yielded benzo[1,2-b:5,4-b′]difuranyl-carbonyl-hydrazono-4-thiazolidinones 9a–f and 10a–f, respectively. Furthermore, the reaction of the thiosemicarbazides with phosphorus oxychloride gave benzo[1,2-b:5,4-b′]difuranyl-1,3,4-thiadiazoles 11a–f. Some compounds in this study were biologically evaluated for their ability to bind to DNA.

SYNTHESIS OF BENZO[1,2-b: 5,4-b′]- DIFURANYL-TRIAZOLES, -OXADIAZOLES, -THIAZOLIDINONES, -THIADIAZOLES, AND THE USE OF DNA IN EVALUATION OF THEIR BIOLOGICAL ACTIVITY

Quinoline-2-carbohydrazide (3) was reacted with aryl or alkyl isothiocyanates to give the corresponding quinoline thiosemicarbazides (4a–e). Cyclization of the substituted thiosemicarbazides with sodium hydroxide led to the formation of 5-(quinolin-2-yl)-2H-1, 2, 4-triazole-3(4H)-thiones (5a–e). Desulfurization of thiosemicarbazides by mercuric oxide gave 5-(quinolin-2-yl)-1, 3, 4-oxadiazol- 2-amines (6a–e). Treatment of thiosemicarbazides with ethyl bromoacetate or α -bromopropionic acid yielded (Z)-N′-(3-substituted thiazolidin-4-oxo-2-ylidene) quinoline-2-carbohydrazides (7a–d), (8a–d), respectively. Treatment of thiosemicarbazides with chloroacetone furnished (Z)-N′-(4-methyl-3-substituted-thiazol-2(3H)-ylidene) quinoline-2-carbohydrazides (9a–d). Furthermore, the reaction of thiosemicarbazides with phosphorus oxychloride gave N-substituted-5-(quinolin-2-yl)-1,3,4-thiadiazol-2-amines (10a–e). All newly synthesized compounds were tested and evaluated for antimicrobial activity.

Synthesis and Reactions of Some New Quinoline Thiosemicarbazide Derivatives of Potential Biological Activity

The base promoted nucleophilic addition of cyanoacetamide derivatives 2a,b to equimolar amount of phenyl isothiocyanate in DMF containing potassium hydroxide afforded the corresponding potassium sulfide salts 3a,b which were not isolated but which underwent heterocyclisation upon treatment with chloroacetyl chloride to give the corresponding 2-cyano-2-(5-oxo-3-phenylthiazolidin-2-ylidene)-acetamide derivatives 4a,b. The reactions of 4a,b with aryl diazonium salts, bromine and aromatic aldehydes were studied in order to obtain compounds 5–11.

Synthesis and reactions of 2-cyano-2-(5-oxo-3-phenyl-thiazolidin-2-ylidene)-acetamides

The novel and versatile enaminones 2a,b were synthesized by treatment of visnaginone methyl ether 1a or khellinone methyl ether 1b with N,N-dimethylformamide dimethylacetal. They were reacted with hippuric acid or N-acetylglycine to yield benzofuran-5-yl-2H-pyran-2-ones 3a–d. The reaction of 2a,b with cyanoacetamide and malononitrile dimer in sodium ethoxide gave benzofuran-5-yl-pyridones 4a,b and [benzofuran-5-yl-1H-pyridine-2-ylidene] malononitrile 5a, respectively. Refluxing 2a,b with hydrazine hydrate or with hydroxyla- mine afforded benzofuran-5-yl-1H-pyrazoles 6a,b and benzofuran-5-yl-isoxazoles 7a,b, respectively. Moreover, 2a,b coupled with aryl diazonium salt in the presence of sodium hydroxide to yield 3-(benzofuran-5-yl)-2-aryl-hydrazono-3-oxo-propanals 8a,b which were excellent precursors for the synthesis of pyridazines 9–12. © 2003 Wiley Periodicals, Inc. 15:85–91, 2004; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10219

https://onlinelibrary.wiley.com/doi/pdf/10.1002/hc.10219

Eman M. Keshk

Papers

Synthesis and evaluation of some new spiro indoline-based heterocycles as potentially active antimicrobial agents.

SYNTHESIS OF BENZO[1,2-b: 5,4-b′]- DIFURANYL-TRIAZOLES, -OXADIAZOLES, -THIAZOLIDINONES, -THIADIAZOLES, AND THE USE OF DNA IN EVALUATION OF THEIR BIOLOGICAL ACTIVITY

Synthesis and Reactions of Some New Quinoline Thiosemicarbazide Derivatives of Potential Biological Activity

Synthesis and reactions of 2-cyano-2-(5-oxo-3-phenyl-thiazolidin-2-ylidene)-acetamides

Benzofuranyl‐pyran‐2‐ones, ‐pyridazines, and ‐pyridones from naturally occurring furochromones (visnagin and khellin)