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.

GRAPHICAL ABSTRACT      

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.

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.

GRAPHICAL ABSTRACT      

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.

GRAPHICAL ABSTRACT      

Regioselective Syntheses of 1-Aryl-substituted-5H-[1,3]thiazolo[3,2-a]quinazoline-5-ones During Sonogashira Coupling

Abstract

Reaction of 2-mercaptopropargylquinazoline-4-one with various aryliodides catalyzed by Pd–Cu leads to the regioselective formation of 1-arylsubstituted-5H-[1,3]thiazolo-[3,2-a]quinazoline-5-ones.

GRAPHICAL ABSTRACT      

Synthesis of Novel Thioethers from Polyhalobutadienes and Thiols

Abstract

Substituted perchlorobutadienes were synthesized from the reactions of hexachloro-1,3-butadiene with some thiols in ethanol in the presence of sodium hydroxide. The oxidation products were obtained from the reactions of thioethers with m-chloroperbenzoic acid. The structures of the new compounds were characterized by microanalysis and spectroscopic data.

GRAPHICAL ABSTRACT      

Trimethylphenylammonium Tribromide as a New and Efficient Oxidizing Agent for the Oxidative Coupling of Thiols into Disulfides and Chemoselective Oxidation of Sulfides into Sulfoxides

Abstract

Trimethylphenylammonium tribromide has been introduced as a versatile and new oxidizing agent for the preparation of disulfides and sulfoxides from thiols and sulfides, respectively. The reaction progress is simple, and proceeds under mild and homogenous conditions in ambient temperature.

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.

GRAPHICAL ABSTRACT      

Eco-Friendly One-Pot Synthesis of 2,4-Disubstituted Thiazoles by Grinding Under Catalyst- and Solvent-Free Conditions

Abstract

An efficient and facile synthesis of 2,4-disubstituted thiazoles is achieved by a one-pot reaction of aldehydes and α-bromoketones with thiosemicarbazide by grinding under catalyst- and solvent-free conditions. This method has notable advantages in terms of simple workup, neat conditions, high yield, reasonably rapid reaction rate, and environmental friendliness.

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.

GRAPHICAL ABSTRACT     

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.

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.

GRAPHICAL ABSTRACT      

Synthesis and Fungicidal Activity of Thiazoline Derivatives Containing Halogenated Indolyl Moiety

Abstract

A series of novel 1,3-thiazoline derivatives containing a 5- or 6-position halogenated indole moiety were synthesized via a one-pot and three-step reaction. Their structures were confirmed by spectroscopic methods. The fungicidal activities of all the title compounds were evaluated. Most of them exhibited moderate to high activity against eight plant pathogens at the concentration of 50 ug/mL. Generally the fungicidal activity of fluorinated indolyl thiazolines was higher than that of chlorinated indolyl thiazoline derivatives.

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.

GRAPHICAL ABSTRACT      

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.

GRAPHICAL ABSTRACT     

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).

GRAPHICAL ABSTRACT     

Succinimide-N-Sulfonic Acid: A Mild,Efficient, and Reusable Catalyst for the Chemoselective Trimethylsilylation of Alcohols and Phenols

Abstract

Succinimide-N-sulfonic acid (SuSA) is easily prepared by the reaction of succinimide with chlorosulfonic acid. This reagent is able to efficiently catalyze the chemoselective trimethylsilylation of alcohols and phenols with hexamethyldisilazane (HMDS). All reactions were performed under mild reaction conditions, giving excellent yields.

GRAPHICAL ABSTRACT      

Superoxide Ion–Promoted Facile One-Pot Synthesis of O-Alkyl-S-methyl Dithiocarbonates from Alcohol Under Mild Reaction Conditions

Abstract

A new, mild, and efficient protocol for the one-pot synthesis of O-alkyl-S-methyl dithiocarbonates (xanthates) has been described in reasonably good yields from a variety of alcohols employing carbon disulfide and methyl iodide using superoxide ion at room temperature.

GRAPHICAL ABSTRACT     

Copper (I) Iodide-Catalyzed Solvent-Free Synthesis of α-Aminophosphonates

Abstract

A method for the synthesis of α-aminophosphonates through the three-component coupling reaction of aldehydes, amines, and diisopropyl phosphite using copper (I) iodide salt catalyst is demonstrated, The reaction is highly efficient, economic, and also environment friendly.

[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, Figures S1–S9.]

GRAPHICAL ABSTRACT