Phase Transfer–Catalyzed,One-Pot Synthesis of Some Novel N-Pyrimidinyl-N′-nicotinyl Thiourea Derivatives

Abstract

A new series of acyl thiourea derivatives were synthesized in one-pot using PEG-600 as the phase transfer catalyst (PTC). The structures of title compounds were characterized by ¹H NMR, IR, MS, and elemental analysis. In addition, the fungicidal activity of the acyl thiourea derivatives were tested, which showed that most of them exhibit moderate activity.

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Synthesis,Dimeric Crystal Structure,and Fungicidal Activity of 1-(4-Methylphenyl)-2-(5-((3,5-dimethyl-1H-pyrazol-1-yl)methyl)-4-phenyl-4H-1,2,4-triazol-3-ylthio)ethanone

Abstract

A new triazole compound, C₄₆H₄₆N₁₀O₂S₂, has been synthesized, and the crystal structure was determined by a single crystal X-ray diffraction study. The fungicidal activity of the title compound was determined, and the results showed that it displays moderate fungicidal activity.

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The Synthesis of Novel S-, S,S-, S,S,S-, and N,S-Substituted Nitrodienes from Polyhalonitrodienes and Thiols

Abstract

The novel S-, S,S-, and S,S,S-substituted nitrobutadienes were synthesized from the reactions of 2-nitrobutadiene compounds with some thiols. The new N,S-substituted nitrobutadienes were obtained from the reaction of the mono-thiosubstituted butadienes with morpholine, thiomorpholine, homopiperazine, and piperazine derivatives. The structures of new compounds were determined by spectroscopic techniques.

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A Simple Synthesis of Oxaphospholes

Abstract

Stable derivatives of oxaphospholes were obtained from the reaction between electron-deficient acetylenic compounds and phenacyl bromide or its derivatives in the presence of triphenylphosphine in acetonitrile as the solvent in excellent yields.

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Synthesis of Dialkyl Phosphorylsuccinates from the Reaction of Thiouracil Derivatives with Dialkyl Acetylenedicarboxylates in the Presence of Trialkylphosphites

Abstract

Dialkyl-2-(dialkoxyphosphonyl)-3-(1,6-dihydro-6-oxo-4-propylpyrimidin-2-ylthio) succinates and dialkyl-2-(dialkoxyphosphonyl)-3-(1,6-dihydro-6-oxopyrimidin-2-ylthio) succinates were synthesized in moderate to high yields using a novel, facile, and one-pot condensation of dialkyl acetylenedicarboxylates, trialkylphosphites, and thiouracil derivatives.

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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.

[Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements for the following free supplemental resource: Table S1]

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Phosphorylation of Acylated Trihydroxybenzene Derivatives by Phosphorous Triamides

Abstract

The phosphorylation of acylated trihydroxybenzene derivatives by amides of phosphorous acid was considered. The possibility of selective phosphorylation of triacetoxy phloroglucin was shown.

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Tin(IV) Complexes of 1,5-Diphenylthiocarbazone and Thiosemicarbazide: Synthesis,X-Ray Characterization,and Biological Activity

Abstract

The reaction of Me₂SnCl₂ with dithizone or thiosemicarbazide produced two novel di-organotin derivatives in good yields, which were characterized by X-ray diffraction. The crystal structures show that the compounds present a distorted pentacoordinated tin(IV) metal center. The antimicrobial activity of the new compounds was studied against Gram-negative (Escherichia coli, Klebsiella pneumonia, Salmonella enteritidis) and Gram-positive (Staphylococcus aureus) bacteria, and the yeast Saccharomyces cerevisiae. It was observed that the coordination of tin metal has a pronounced effect on the microbial activities of the ligands. All the tin complexes have shown higher antimicrobial effect than the free ligands.

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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 of New Benzylic Di-, Tri-, and Tetraphosphonic Acids as Potential Chelating Agents

Abstract

New di-, tri-, and tetraphosphonic acids were synthesized starting from four o-hydroxymethyl phenol derivatives and obtained in three steps in good overall yield. The phosphonic acids were isolated and purified using semi-preparative C₁₈ HPLC column. The new compounds were characterized using different spectroscopic methods (¹H, ¹³C, and ³¹P NMR; ESI MS; and MSⁿ, IR).

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Reaction of 1-Aryl-1H-1,2,3-Triazole-4-Carbonyl Chlorides/Isothiocyanates with 3-Amino-5-Methylisoxazole

Abstract

1-Aryl-1H-1,2,3-triazole-4-carbonyl chlorides were selected as starting materials for the Boulton–Katritzky rearrangement. When 3-amino-5-methylisoxazole was acylated by 1-aryl-1H-1,2,3-triazole-4-carbonyl chlorides, 1-aryl-5-methyl-N-(5-methylisoxazol-3-yl)-1H-1,2,3-triazole-4-carboxamides 5 were obtained and no further rearrangement occurred. On the other hand, when 1-aryl-1H-1,2,3-triazole-4-carbonyl chlorides were first converted into isothiocyanates by the reaction with KSCN and then were allowed to react with 3-amino-5-methylisoxazole 4 in one pot, intermediate thioureas were formed and spontaneously transformed in statu nascendi into 1,2,4-thiadiazole derivatives 6.

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Phosphorylation of Dienyl Diprenoid Alcohols

Abstract

The reactions of geraniol, nerol, and linalool with N,N-diethylamido O,O-propylenephosphite and diethyl chlorophosphite were studied. On the basis of these studies, new dienyl diprenoid phosphite esters were obtained.

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