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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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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A Facile Synthesis of 3H-Benzo[1,2]Dithiole-3-Thiones and Their Condensation with Active Methylene Compounds

Abstract

3H-Benzo[1,2]-dithiole-3-thiones were prepared from potassium sulfide and 2-halobenzaldehydes in moderate-to-good yields, and a plausible mechanism for this catalyst-free intramolecular heteroannulation reaction has been proposed. The Knoevenagel condensation reactions of 3H-benzo[1,2]dithiole-3-thiones with active methylene compounds such as ethyl 2-cyanoacetate and diethyl malonate, and the three-component one-pot reactions of potassium sulfide, 2-halobenzaldehydes, and ethyl 2-cyanoacetate, affording the corresponding products, have been developed.

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A Practical and Eco-Friendly Method for Conversion of Epoxides to Thiiranes with Immobilized Thiourea on CaCO3

Abstract

Solvent-free conversion of various epoxides to the corresponding thiiranes was carried out efficiently with immobilized thiourea on CaCO₃. The reactions were completed within 1–12 min under oil bath (60 °C–70 °C) conditions to afford thiiranes in 88%–98% yields.

[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: Figures S1–S3.]

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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.

[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: Selected Data.]

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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.

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Efficient Syntheses of 1H-Isochromen-1-Ylmethylphosphonates via Regioselective 6-Endo-Dig Addition to Carbon—Carbon Triple Bond Catalyzed by Pd(OAc)2

Abstract

An efficient, regioselective, palladium-catalyzed intramolecular cycloisomerization of dialkyl [(2-(2-ethynyl)phenyl)(2-hydroxyl)ethyl]phosphonate 6 is reported. The reactions proceed through a 6-endo-dig cyclization to afford 1H-isochromen-1-ylmethylphosphonates 7 in good to excellent yields using palladium(II) acetate as the catalyst in tetrahydrofuran at room temperature.

[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: General Comments. Figures S1–S33.]

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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.

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Chiral Phosphoric Acid Catalyzed Asymmetric Friedel–Crafts Alkylation of Indoles with Nitroolefins

Abstract

Asymmetric Michael-type Friedel–Crafts (F–C) alkylations of indoles with nitroolefins catalyzed by a chiral H₈-BINOL-based phosphoric acid were investigated. The reactions took place very smoothly in the presence of only 5 mol-% of catalyst at room temperature to afford the desired F–C alkylation products in good yields and with moderate enantioselectivities.

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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.

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One-Pot Synthesis of Novel Rhodanine Based Ketenimines Via Multicomponent Reactions

Abstract

Synthesis of polyfunctionalized ketenimines via three-component reactions of rhodanine and 5-(4-dimethylaminobenzylidene)-rhodanine with dialkyl acetylenedicarboxylates and alkyl isocyanides is described. The reactions proceed smoothly under mild conditions leading to the desired products in good yields. In the case of methyl acetylenecarboxylate, the reaction led to methyl (Z)-3-({5-[(E)-1-(tert-butylamino)methylidene]-4-oxo-4,5-dihydro-1,3-thiazol-2-yl}sulfanyl)-2-propenoate in low yield.

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Synthesis and Characterization of Novel Alkyl-Substituted Aryl Diphenylphosphinate Esters

Abstract

In this work, the reactions of diphenylphosphinic chloride, (C₆H₅)₂P(O)Cl, 1, with the sodium salts of sterically hindered phenol derivatives (2a-2j) were investigated. Novel alkyl-substituted aryl diphenyl phosphinate esters (C₆H₅)₂P(O)OAr (3-12) were obtained from these reactions. Satisfactory analytical and spectroscopic results were obtained for all the new compounds.

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A Novel and Efficient Synthesis of α-Aminophosphonates by Use of Triphenyl Phosphite in Acetic Acid Media

Abstract

For the first time, α-aminophosphonates were obtained by a simple and efficient one-pot method from the reaction between aldehyde, aniline, and triphenyl phosphite in the presence of acetic acid as a catalyst and solvent at room 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.

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