Synthesis and Properties of 2-Alkylene/Dialkyl Dithiophosphato-2-oxo-1,3,2-dioxaphosphorinanes

Reactions of 2-chloro-2-oxo-1,3,2-dioxaphosphorinanes with ammonium alkylene/dialkyl dithiophosphates in a 1:1 molar ratio in refluxing benzene solution yields nonvolatile, yellow viscous liquids of the type (S)S(O) and (RO)₂ P(S)S(O) , respectively. [G = ? CH₂CH₂CHCH₃?,. ? C(CH₃)₂CH₂CHCH₃?,. ? CH₂C(CH₃)₂CH₂; R = i-C₃H₇, C₂H₅].

These compounds are hygroscopic and monomeric in nature. The newly synthesized derivatives have been characterized by physicochemical and spectroscopic techniques (IR, NMR [¹H&³¹P], and M.W).     

Ionic Liquid Promoted Efficient Three-Component Synthesis of 2-Thioxo-2H-Thiopyrans

Abstract

An efficient one-pot three-component method for the synthesis of a variety of 2-thioxo-2H-thiopyrans has been described. Fairly good yields are obtained by cyclization reactions of arylidenemalononitriles, derived in situ from ketones and malononitrile, with carbon disulfide in the presence of a base in the ionic liquid 1-butyl-3-methylimidazolium bromide as reaction medium.

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One-Pot Green Synthesis of 3'-(2-Aminobenzimidazolyl)-2-Phenyl Spiro[4H-Benzopyran-4,2'-Thiazolidin]-4-Ones and Acylation Using Trifluoroacetic Anhydride

Abstract

An expeditious one-pot synthesis of a novel heterocyclic system, 3′-(2-aminobenzimidazolyl)-2-phenyl spiro[4H-benzopyran-4,2′-thiazolidin]-4-ones, has been accomplished by condensing substituted hydrazinobenzimidazole, flavanone, and mercaptoacetic acid by conventional heating in ethanol or toluene, and in an ionic liquid, viz., 1-butyl-3-methyl-imidazolium hexafluorophosphate. Excellent yields (85%–90%) and higher purity are obtained in the ionic-liquid-mediated synthesis as compared with the conventional procedure (55%–60%). Further, these compounds were acylated with trifluoroacetic anhydride. The structures of the compounds were confirmed by IR, ¹H NMR, ¹³C NMR, mass spectral data, and elemental analysis. The compounds, upon evaluation for their antibacterial, antifungal, and insecticidal activities, exhibited excellent results.

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Synthesis and Characterization of [1,2,4,6]Thiatriazino[2,3-a][1,3]benzimidazol-1(2H)-one and [1,3,5]Thiadiazino[3,4-a][1,3]benzimidazol-2-imine

Abstract

The reaction of thionyl chloride with amidines 2, derived from N-benzimidazol-2-yl imidates 1, leads to [1,2,4,6]thiatriazino[2,3-a][1,3]benzimidazol-1(2H)-one 3 in good yields. [1,3,5]Thiadiazino[3,4-a][1,3]benzimidazol-2-imine 4 was prepared by condensation of NaSCN with benzimidazol-2-yl imidate 1. The isolated compounds 3 and 4 were identified by spectroscopic methods including IR, ¹H NMR, and ¹³C NMR as well as elemental analyses and MS of 3d and 4b.

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A Convenient Synthesis of Thiazolidin-2-ones from Thiazolidine-2-thiones: Antibiotic Activity and Revisiting the Mechanism

Abstract

Various substituted thiazolidin-2-ones were synthesized from the corresponding thiazolidine-2-thiones with bromoethanol in ethanol with sodium ethoxide as a base. The optimal reaction conditions and mechanism were reinvestigated in detail. The bioassay indicated that (S)-4-isobutyl and (S)-4-benzylthiazolidin-2-ones show certain inhibitive activities against Candida albicans and Escherichia coli.

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An Efficient and Convenient Protocol for the Synthesis of Thiazolidin-4-Ones

Abstract

Without a catalyst and under solvent-free conditions, 2,3-disubstituted-1,3-thiazolidin-4-one 5a–j derivatives were synthesized efficiently via the three-component reaction of aryl hydrazide, aromatic aldehyde, and mercaptoacetic acid. All the newly synthesized compounds were confirmed by IR, ¹H NMR, and ¹³C NMR spectroscopy and elemental analysis.

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Synthesis and Antimicrobial Activity of Some New 5-(3-Chloro-1-Benzothiophen-2-YL)-1,3,4-Oxadiazole-2-Thiol and Their Derivatives

Abstract

3-Chloro-1-benzothiophene-2-carbonylchloride 1 was made to reacts with hydrazine hydrate afforded 3-chloro-1-benothiophene-2-carbohydrazide 2 in good yield. 5-(3-chloro-1-benzothiophen-2-yl)-1,3,4-oxadiazole-2-thiol 4 was synthesized from 3-chloro-1-benzothiophene-2-carbohydrazide 2. Mannich bases, alkyl halide, and acid chlorides derivatives were then prepared. Compound 4 on condensation with chloroacetone in the presence of NaOH as base and ethanol as solvent gave 1-{[5-(3-chloro-1-benzo[b]thiophen-2-yl)-1,3,4-oxadiazol-2-yl]sulfanyl}propan-2-on 6. Condensation of compound 6 with various aromatic aldehydes afforded a series of chalcones 7a–h. The structures of all the synthesized compounds were confirmed by spectral data and have been screened for antibacterial activity.

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New Routes to β-Iminophosphonates,Phosphineoxides, and Sulfides

Abstract

Two synthetic methods leading to β-iminophosphonates, phosphineoxides, and sulfides 2 are reported. The first method involves the reaction of imines with chlorophosphines and phosphites followed by oxidation or sulfurization. The second one utilizes the reaction of imines with diethylchlorophosphate and thiophosphate. The stereochemistry of the obtained products is discussed, and their structure is confirmed by NMR (¹H, ³¹P, ¹³C) and IR spectroscopies, and by mass spectrometry.

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Molecular Iodine as a Versatile Reagent for the Synthesis of Thiazoloquinoline—A Potential Antibacterial Agent

Abstract

A series of 3-(2-aminothiazol-4-yl)quinolin-2[1H]-ones 3 was prepared by neat reaction of quinolin-2[1H]-ones 1 with thioureas 2 in the presence of molecular iodine. The synthesized compounds were evaluated for their in vitro antimicrobial activities against Escherichia coli, Paedococcus sp., Lactobacillus, Yersinia enterocolitica, and Staphylococcus aureus. The green chemical approach for the synthesis of thiazoloquinolinone 3 was performed under neat conditions using molecular iodine as catalyst as well as reaction medium.

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Functionalized Tetrastannacyclobutanes,Part II: Halogeno Substituted Tetrastannacyclobutanes

Abstract

The reaction of 1,1,2,2,3,3,4-hepta-^tbutyl-1-(chloromagnesio)tetrastannacyclobutane with 1,2-halogenopropane leading to halogeno substituted four membered tin ring systems is presented. In addition, the crystal structures of the chloro and the bromo substituted tetrastannacyclobutanes will be discussed.

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Synthesis and Biological Evaluation of Novel Phosphonates Derivatives of As Potential Antitumor Agents

Abstract

A series of dialkyl [2-(4,6-dimethoxypyrimidin-2-yloxy)benzamido](aryl) methylphosphonates derivatives were designed and synthesized. All the new compounds were identified by elemental analysis, IR, ¹H NMR, ³¹P NMR, and MS. Their antitumor activity against KB and CNE1 cells was examined. Some of the compounds showed potential antitumor activity, which provided some hints for further study of structure modification. In particular, the compounds 6i and 6j displayed more potent cytotoxic activities against KB in comparison with 5-FU.

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Solvent-Assisted Naked Eye Sensing of Hg2+ by a Chemoreceptor Derived from Diazocoupling of Sulfathiazole with Diethyl Malonate

Abstract

2-{[4-(Thiazol-2-ylsulfamoyl)-phenyl]-hydrazono}-malonic acid diethyl ester (R1) and 2-{[4-(5-methyl-isoxazol-3-ylsulfamoyl)-phenyl]-hydrazono}-malonic acid diethyl ester (R2) were synthesized through diazocoupling of sulfathiazole and sulfamethoxazole, respectively, with diethyl malonate. They were characterized through various spectroscopic and mass spectral studies. R2 was also characterized through a single crystal X-ray diffraction (XRD) study. Only R1 selectively recognized Hg²⁺ from a wide range of metal ions through naked-eye change. A color change from orange to olive green was observed upon addition of 1.0 equivalent of Hg²⁺ as its chloride salt to the 1 × 10^?3 M DMSO solution of R1. The role of DMSO in the sensing process appears to be the crucial one, because the solvent-assisted band of R1 at 482 nm observed in its UV-Vis spectrum in DMSO did not appear in its spectra recorded in nujol or in a polar aprotic solvent. The UV-Vis and ¹H NMR titrations revealed that the formation of six-membered 1:1 chelate between R1 and Hg²⁺ triggering the desolvation of R1

as the key step towards its sensing activity. The determination of binding stoichiometry between R1 and Hg²⁺ along with binding constant has also been discussed.

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Synthesis of Phosphorylated Enaminoketones and Their Application in the Preparation of Trifluoromethyl-Functionalized 2-Phosphonopyrroles

Abstract

New trifluoromethyl-functionalized 2-phosphonopyrroles were obtained by 5-exotrig cyclization of trifluoromethyl and phosphonyl functionalized enaminoketones.

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Planar Chiral and Achiral Arenido(triphenylphosphane)nickel(II) Complexes Containing N,O Bidentate Ligands: 19F, 1H,and 31P NMR Studies

Abstract

Planar chiral and achiral arenido(triphenylphosphane)nickel(II) complexes (arenido = mesitylenido, 2-toluenido) comprising electronically delocalised N,O chelating ligands were studied by ¹H and ¹⁹F NMR using 1D and 2D techniques. Results from complexes and corresponding ligands are discussed in the light of molecular structures obtained from X-ray diffraction.

GRAPHICAL ABSTRACT