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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Efficient Route for the Synthesis of New Dinaphthosulfoxide Aza Crowns Using Ethyleneglycol Under Microwave (MW) Irradiation: Macrocyclization is Preferred to Oligomerization Under MW Irradiation

Abstract

New dinaphthosulfoxide aza crowns were prepared from the corresponding dinaphthosulfoxide diester and diamines under reflux conditions (conventional heating) and microwave (MW) irradiation. These reaction routes were used for the synthesis of a series of aza crowns, such as dinaphthosulfide, dinaphthosulfone, dibenzosulfide, and dibenzosulfoxide. The synthesis of aza crowns under MW irradiation in comparison with conventional heating has several advantages, such as shorter reaction times, simpler reaction conditions, and the use of ecofriendly solvents, higher yields, and regioselectivity. In the MW synthesis, macrocyclization is preferred to oligomerization, and thus, the yields of byproducts are low.

Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.

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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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A Convenient Synthesis of 2-Amino-1,3- selenazoles Using Ionic Liquid and Microwave Irradiation

Abstract

A simple and environmentally benign synthesis of 2-amino-1,3-selenazoles by microwave irradiation using 1-butyl-3-methylimidazolium tetrafluoroborate ([Bmim]BF₄) ionic liquid (IL) is described. Acyl halides, phenacyl halides, and α-bromo-β-keto esters easily undergo condensation with selenourea in ([Bmim]BF₄) by microwave irradiation to afford the desired products of good purity in excellent yields. The ionic liquid can be easily recovered and reused at least 10 times without losing its activity. The duration of the reaction ranges from 4–6 min.

Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.

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Synthesis,Characterization, and Biological Screening of Some Novel Thiazolidin-4-One and α-Aminophosphonate Derivatives

Abstract

Synthesis of some new functionalized thiazolidin-4-ones and α-amino phosphonate derivatives has been reported. The imines were synthesized from the reaction of various substituted anilines with 1-phenyl-3-(pyridine-4-yl)-1H-pyrazole-4-carbaldehyde in ethanol at reflux condition. The corresponding thiazolidin-4-ones and α-aminophosphonates were prepared by reaction of imines with mercaptoacetic acid and triethyl phosphite, respectively. The structures of the newly synthesized compounds were confirmed by IR, ¹H NMR, and mass spectral data and were evaluated for their antimicrobial activities.

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Efficient Uncatalyzed Conversion of Primary and Secondary Thioamides into 1-Substituted, 5-Substituted, 1, 5-Disubstituted and Annulated Tetrazoles

Abstract

Unprecedented high-yield simple and mild conversion of primary aliphatic and aromatic thioamides into 5-substituted tetrazoles on treatment with a combination of tetrachlorosilane and sodium azide in refluxing acetonitrile has been achieved. Secondary acyclic, cyclic, and heterocyclic thioamides could also be transformed in high yields into 1-substituted, 1,5-disubstituted, or annulated tetrazoles under the same reaction condition.

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Preparation of α-Ketophosphonate Derivatives and Their Application in the Synthesis of 1-(N-Alkylcarbamoyl)-1-(diethoxyphosphoryl)alkyl Benzoates via Passerini Reaction

Abstract

The Passerini reaction of α-ketophosphonates, isocyanides, and benzoic acid derivatives leads to 1-(N-alkylcarbamoyl)-1-(diethoxyphosphoryl)alkyl benzoates in one step at room temperature. The structures of products were assigned on the basis of their ¹H NMR, ¹³C NMR, ³¹P NMR, and IR spectroscopic data.

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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.

Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.

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Addition of Sulfinic Acids to Methacrylic Derivatives

Abstract

The kinetics of the addition of arenesulfinic acids to methacrylic derivatives were studied. The reactions were found to be second order over a range of concentrations from 0.01 to 0.10 M. For pH values ranging from 4 to 8, the following rate constants were obtained pH the methylacrylate, chloromethylacrylate, and bromomethylacrylate with benzenesulfinic acids (278 K) were investigated: 2.37 (± 0.2).10^?4 M^?1s^?1, 2.60 (± 0.1).10^?4 M^?1s^?1, 3.15 (± 0.3).10^?4 M^?1s^?1.

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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 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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Microwave-Assisted Direct Synthesis of 4H-1,2,4-Benzothiadiazine 1,1-Dioxide Derivatives

Abstract

We describe a rapid and convenient methodology for the preparation of diverse 3-aryl and 3-trifluoromethyl 4H-1,2,4-benzothiadiazine-1,1-dioxides in a one-pot microwave-promoted reaction between 2-aminobenzenesulfonamides and benzaldehydes, trifluoroacetic acid or benzoic acids.

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Simple and Efficient Synthesis of 1,3-Dithioles with Pyrimidinylidene or Pyrazolylidene Substituents

Abstract

2-Pyrimidinylidene-1,3-dithioles or 2-pyrazolylidene-1,3-dithioles are prepared by a three-component condensation reaction of pyrimidine-tetraone or 1H-pyrazole-4,5-dione, carbon disulfide, and dialkyl acetylendicarboxylates in the presence of tributylphosphine.

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