Convenient One-Pot Research Articles

A Convenient One-Pot Process for Converting Thiols into Sulfonyl Fluorides Using H2O2 as an Oxidant

AbstractA novel protocol for synthesizing sulfonyl fluorides from thiols in one pot is reported. Utilizing SOCl2 and H2O2 as low-cost and convenient reagents allows the direct oxidative chlorination of readily available thiol derivatives to give the corresponding sulfonyl chlorides, with subsequent fluoride–chloride exchange mediated by KHF2 giving access to the desired sulfonyl fluorides. This transformation features mild conditions, operational simplicity and high efficiency, and utilizes a broad substrate scope, including a variety of aryl, alkyl, benzyl and heteroaryl thiols.

Convenient One-Pot Synthesis of Kynurenic Acid Ethyl Ester and Exploration to Direct Synthesis of Neuroprotective Kynurenic Acid and Amide Derivatives.

Kynurenic acid (KYNA) is an endogenous molecule, which is a non-selective antagonist of ionotropic glutamate receptors and has been found to have neuroprotective activity. A supplement of KYNA may be applicable for the treatment of neurodegenerative disease, but it does not cross the blood-brain barrier due to its polar nature. Therefore, its different esters and amide derivatives were explored as a prodrug, which can cross blood-brain barrier and transform into KYNA in situ. However, many esters and amide derivatives of KYNA are synthesized via coupling reaction or multi-step synthesis using different organic or metallic catalysts. Herein, we developed a novel one-pot, catalyst-free, convenient synthesis of KYNA ethyl esters using aniline and diethyl acetylene dicarboxylate in DMF under heating. We also explored the synthesis of KYNA and KYNA amide derivative in a simple manner with overall good yields via hydrolysis and condensation, respectively.

Total Synthesis of Lucidumone through Convenient One-pot Preparation of the Tetracyclic Skeleton by Claisen Rearrangement and Subsequent Intramolecular Aldol Reaction.

The total synthesis of lucidumone (1), a Ganoderma meroterpenoid, was accomplished in racemic form from easily prepared 6 and 7 in 10 steps as the longest linear sequence. The synthesis was completed through one-pot preparation of the tetracyclic core skeleton by Claisen rearrangement followed by an intramolecular aldol reaction. The intramolecular aldol reaction allowed for the stereocontrolled construction of the bicyclo [2.2.2] octane skeleton fused to an indanone structure. The enantioselective total synthesis of 1 was also described via a chiral transfer strategy in the Claisen rearrangement.

Convenient One-Pot Synthesis of 9H-Carbazoles by Microwave Irradiation Employing a Green Palladium-Based Nanocatalyst

AbstractAn efficient palladium-catalyzed tandem reaction for the one-pot synthesis of 9H-carbazoles under microwave irradiation is developed. This approach involves a sequential Buchwald–Hartwig amination and a direct arylation from affordable and inexpensive anilines and 1,2-dihaloarenes. For the development of this purpose, a novel and magnetically recoverable palladium nanocatalyst supported on a green biochar under ligand-free conditions is used. Compared to other existing palladium-based protocols, the present synthetic methodology shows a drastic reduction in reaction times and excellent compatibility with different functional groups allowing to obtain a small library of 9H-carbazoles in high yields and with good regioselectivity. This procedure represents the first example in the direct synthesis of carbazoles using a heterogeneous palladium nanocatalyst from commercial precursors. To examine the application of this protocol, a direct and scalable synthesis of the bioactive carbazole alkaloid clausenalene from commercially available starting materials is described.

A Convenient One-Pot Synthesis of Chalcones and Their Derivatives and Their Antimicrobial Activity

A series of chalcones were synthesized by base-catalyzed Clasien-Schmidt condensation of substituted benzaldehydes and substituted acetophenones at room temperature. The addition of hydrazine hydrate and hydroxylamine hydrochloride across the double bond of the obtained chalcones gave pyrazole and isoxazole derivatives, respectively. All the synthesized compounds were characterized by 1H and 13C NMR and FT-IR spectroscopy and screened for their in vitro antimicrobial activity against two bacterial strains, Pseudomonas aeruginosa and Pseudomonas oryzihabitans using Ciprofloxacin as standard drug. 1-(2-Methoxyphenyl)-3-phenylprop-2-en-1-one and 1-(4-chlorophenyl)-3-phenylprop-2-en-1-one showed significant activity against both bacterial strains and hence proved to be potent antimicrobial agents.

A Convenient One-Pot Synthesis of 1,5-Disubstituted Tetrazoles Containing an Amino or a Carboxy Group

A convenient method is proposed for constructing the tetrazole ring by a one-pot reaction of amides with phosphorus oxychloride and sodium azide. A series of 1,5-disubstituted tetrazoles containing an amino or a carboxy group, which present interest as buildings blocks for the synthesis of biologically active substances, were obtained.

Facile, one-pot, four-component synthesis of a new series of imidazo[1,2-a]pyridines in presence of TPAB in EtOH under reflux conditions

A convenient, regioselective, novel, and elegant one-pot, four-component reaction was designed for synthesis of a series of new of imidazo[1,2-a]pyridines using aryl glyoxal monohydrates, ethyl acetoacetate, hydrazine hydrate, and 2-aminopyridine in presence of tetrapropylammonium bromide under reflux in EtOH as solvent. The main advantages of this protocol include the availability and low cost of the starting materials, short reaction time, convenient operation, easy workup process, highly facile operation, nonhazardous byproducts, and high yield (82–94%).

Convenient One-Pot Two-Step Synthesis of Symmetrical and Unsymmetrical Diacyl Ureas, Acyl Urea/Carbamate/Thiocarbamate Derivatives, and Related Compounds

A wide range of chemicals such as amides, hydrazides, amines, alcohols, carbazate, and sulfonate were reacted with acyl isocyanates generated by the reaction of primary amides with oxalyl chloride to give symmetrical and unsymmetrical diacyl urea derivatives, acyl ureas/carbamates/thiocarbamates, and related compounds. This method provides means for convenient one-pot, two-step synthesis of compounds bearing urea, carbamate, and other functional groups from cheap and commercially available starting reagents. It is expected that the results presented in this report will expand the medicinal chemist’s toolbox.

ChemInform Abstract: Cu(I)‐Promoted One‐Pot Click‐SNAr Reaction of Nitrobenzaldehydes.

ABSTRACTA series of 1,4-disubstituted 1,2,3-triazoles containing formyl was synthesized from a variety of readily available nitrobenzaldehydes and alkynes via a convenient one-pot, click-SNAr reaction with moderate to excellent yields. The reactions were easily carried out in hexamethyl phosphoramide in the absence of a base at 60 °C.

Cu(I)-promoted one-pot click-SNAr reaction of nitrobenzaldehydes

ABSTRACTA series of 1,4-disubstituted 1,2,3-triazoles containing formyl was synthesized from a variety of readily available nitrobenzaldehydes and alkynes via a convenient one-pot, click-SNAr reaction with moderate to excellent yields. The reactions were easily carried out in hexamethyl phosphoramide in the absence of a base at 60 °C.

Convenient One-Pot Synthesis of Spirooxindole Derivatives Containing a 1,3,4-Thiadiazine Scaffold

A useful strategy for the construction of spirocyclic oxindoles bearing a 1,3,4-thiadiazine skeleton is reported. The desired products were obtained in high yields under mild conditions.

Ethanepolyphosphonates: Convenient One-Pot Syntheses of Esters, Acids, and Salts with High Yields and Their Properties

Polyfunctional phosphonates CHP*2–CHP*2, CH2P*–CHP*2, CHR′P*–CHP*2 (P* = P(O)(OR)2; R = Me, Et, iPr, iOct; R′ = Ph, Mes, CH2P*) were synthesized from chlorinated ethylenes by reaction with sodium dialkyl phosphites (RO)2PONa in THF using convenient one-pot procedures. Some corresponding acids (R = H) of general type HnL and salts were described. Molecular structures were deduced from NMR and X-Ray studies. Noncanonical rotamers in overcrowded molecules are discussed.

A novel reduction approach to fabricate quantum-sized SnO2-conjugated reduced graphene oxide nanocomposites as non-enzymatic glucose sensors

Quantum-sized SnO2 nanocrystals can be well dispersed on reduced graphene oxide (rGO) nanosheets through a convenient one-pot in situ reduction route without using any other chemical reagent or source. Highly reactive metastable tin oxide (SnO(x)) nanoparticles (NPs) were used as reducing agents and composite precursors derived by the laser ablation in liquid (LAL) technique. Moreover, the growth and phase transition of LAL-induced SnO(x) NPs and graphene oxide (GO) were examined by optical absorption, X-ray diffraction, X-ray photoelectron spectroscopy, Raman spectroscopy and high-resolution transmission electron microscopy. Highly dispersed SnO(x) NPs can also prevent rGO from being restacked into a multilayer structure during GO reduction. Given the good electron transfer ability and unsaturated dangling bonds of rGO, as well as the ample electrocatalytic active sites of quantum-sized SnO2 NPs on unfolded rGO sheets, the fabricated SnO2-rGO nanocomposite exhibited excellent performance in the non-enzymatic electrochemical detection of glucose molecules. The use of LAL-induced reactive NPs for in situ GO reduction is also expected to be a universal and environmentally friendly approach for the formation of various rGO-based nanocomposites.

Convenient One-Pot Three-Component Synthesis of Trifluoromethylated Tetrahydrobenzo[g]chromene Derivatives

A series of ethyl 4-(het)aryl-5,10-dioxo-2-hydroxy-2-(trifluoromethyl)-3,4,5,10-tetrahydro-2 H -benzo[ g ]chromene-3-carboxylates were efficiently synthesized from 2-hydroxynaphthoquinone, aromatic aldehydes, and ethyl 4,4,4-trifluoro-3-oxobutanoate by a one-pot multicomponent reaction catalyzed by the combination of ammonium acetate and acetic acid. The benzochromenes are presumably formed through an initial Knoevenagel condensation followed by a Michael addition and regioselective intramolecular annulation. The dehydration reaction of the hemiketal moiety to the corresponding dehydrated product was also studied.

Convenient One-Pot Synthesis of Chromone Derivatives and Their Antifungal and Antibacterial Evaluation

A one-pot method for the synthesis of chromone derivatives from the reaction of 2-hydroxyacetophenones with aliphatic or aromatic acid chlorides is reported. Esterification and Baker–Venkataraman rearrangement were promoted by t-BuOK, which was followed directly by acid-catalyzed cyclization in one pot. Some of 2-cyclohexyl- and 2-cyclohexylmethyl-substituted chromones displayed activity against plant pathogenic fungal strains. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications® to view the free supplemental file.

Convenient One-Pot Synthesis of Spirooxindole-4H-pyrans in the Presence of SBA-Pr-NH2 and Evaluation of their Urease Inhibitory Activities

A simple and efficient one-pot three-component synthesis of the biologically important spirooxindole-4H-pyrans was carried out by the reaction of isatin, activated methylene reagents, and 4- hydroxycoumarin in aqueous medium. SBA-Pr-NH2 was found to be an efficient heterogeneous nanoporous solid basic catalyst (pore size of 6 nm) which can be easily handled and removed from the reaction mixture by simple filtration. This method is of great value because of its environmentally benign character, high yield processing, and easy handling. The biological activity of target compounds was screened by evaluation of their urease enzyme inhibition

A Convenient One-Pot Preparation of 2-Methyl-3-(phenylthio- methyl)quinolines from Morita-Baylis-Hillman Adducts and Their Oxidation to the Corresponding Sulfones

A convenient one-pot preparation of 2-methyl-3-(phenylthiomethyl)quinolines from Morita-Baylis-Hillman adducts via conjugate addition of thiols followed by reductive cyclization with Fe/AcOH was developed. The 2-methyl-3-(phenylthiomethyl)quinolines were transformed into 2-methyl-3-(phenylsulfonylmethyl)quinolines via m-CPBA-mediated oxidation.

Convenient One-Pot Synthesis of 2,4,5-Triaryl-1H-imidazoles from Arylaldehydes, Benzyl Alcohols, or Benzyl Halides with HMDS in the Presence of Molecular Iodine

A one-pot efficient procedure for the synthesis of 2,4,5-triaryl-1H-imidazole derivatives in good to excellent yields by reaction between hexamethyldisilazane and arylaldehydes, benzyl alcohols, benzyl halides in the presence of molecular iodine has been developed. The remarkable advantages of this method are the simple workup procedure, high yields of products, and the availability of reagents.

Facile and Convenient One-Pot Process for the Synthesis of Spirooxindole Derivatives in High Optical Purity Using (−)-(S)-Brevicolline as an Organocatalyst

The paper presents an application of the asymmetry approach to spirooxindoles via Brevicolline, Cinchonidine or Cinchonine catalyzed one-pot multicomponent synthesis. Brevicolline, in comparison with Cinchonidine or Cinchonine, catalyzes the reaction of isatins, acetylacetone/ethyl 3-oxobutanoate and malononitrile, with the formation of spiro[oxindole-3,4'-4'H-pirane] derivatives in an optically active form in very good to excellent yields.

ChemInform Abstract: Mild and Convenient One-Pot Synthesis of β-Lactams by Condensation of Titanium Enolates of 2-Pyridylthioesters with Imines.

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