Efficient and Convenient Methods for Synthesis of Some Phthalazine Derivatives and Their Evaluation of Cytotoxicity

A systematic study of the reaction of 1,4-dihydrazinophthalazine (DHPH) with 1,3-dicarbonyls [viz., acetylacetone (acac), dibenzoylmethane (bzbz), and 1-benzoylacetone (bzac)] varying the reaction conditions was carried out to obtain the phthalazine derivatives (1–4). One-pot reaction of DHPH with acac led to the formation of two compounds 1 and 2, with various factors such as the presence of the acid or base, amount of the acac, time of reflux, and the temperature. The reaction conditions of DHPH with bzbz or bzac are sort of different to isolate the products 3 and 4, respectively. The derivatives (1–4) have been characterized by elemental analyses, ¹H NMR, and electrospray ionization–mass spectrometry (ESIMS) and the cytotoxic activity of the compounds 1–4 was evaluated on HeLa cell line.

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Efficient Synthesis of Some New 2,3-Dimethylquinoxaline-1-oxides Using Bis(acetoxy)phenyl-λ 3-iodane as an Oxidant

A series of 2-(arylimino)-3-(hydroxyimino)butanes 3a–g, easily accessed by the condensation of variously substituted anilines 1a–g with biacetyl monoxime 2, were efficiently cyclized to afford 2,3-dimethylquinoxaline-1-oxides 4a–g using bis(acetoxy)phenyl-λ ³-iodane as an oxidant. This methodology utilizes a commercially available and environmental benign oxidant to achieve the title compounds in excellent yields under mild conditions.

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Synthesis,Antibacterial, and Antifungal Activities of Imidazo[2,1-c][1,2,4]triazoles and 1,2,4-Triazolo[4,3-a]pyrimidinones

A straightforward method has been developed for the synthesis of 1-phenyl-imidazo [2,1-c][1,2,4]triazole derivatives 5a–j and 1-phenyl-[1,2,4]triazolo[4,3-a]pyrimidinones derivatives 6a–g starting from 5-amino-1-phenyl[1,2,4]triazole and p-toluenesulfonic acid (PTSA). This methodology affords a number of 1-phenyl-imidazo [2,1-c][1,2,4]triazoles 5a–j and 1-phenyl-[1,2,4]triazolo[4,3-a]pyrimidinones 6a–g in reasonable yields and short reaction times. The structures of all new compounds were elucidated using infrared, ¹H and ¹³C NMR, and high-resolution mass spectrometry. Some of the newly synthesized compounds were screened for their antimicrobial activity.

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Evaluation of Baylis–Hillman Routes to 3-(Aminomethyl)coumarin Derivatives

The relative merits of two different Baylis–Hillman approaches toward the preparation of coumarin derivatives, containing peptide-like side chains, have been explored. In one approach, use of methyl acrylate as the activated alkene requires a protecting group strategy, an approach that is not necessary when using tert-butyl acrylate.

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5-Ethoxymethylidene-4-thioxo-2-thiazolidinone as Versatile Building Block for Novel Biorelevant Small Molecules with Thiopyrano[2,3-d][1,3]thiazole Core

5-Ethoxymethylidene-4-thioxo-2-thiazolidinone was studied as versatile core building block in the synthesis of new thiopyrano[2,3-d]thiazole derivatives relevant for medicinal chemistry purposes under hetero-Diels–Alder reaction conditions. Promising compounds (6, 10) were identified among synthesized series with high antitumor and moderate antiviral activity.

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Synthesis and Spectral and Electrochemical Characterization of Novel Substituted 1,4-Naphthoquinone Derivatives

The novel substituted 2,3-dichloro-1,4-naphthoquinone derivatives were synthesized from the reactions of (1) and related nucleophilles in sodium carbonate (Na₂CO₃) solution of ethanol, chloroform with Et₃N, or potassium carbonate (K₂CO₃) solution of acetonitrile. The structures of novel compounds were characterized by using microanalysis, Fourier transform–infrared, ¹H NMR, ¹³C NMR, mass spectrometry, and cyclic voltammetry (CV).

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Synthesis of Supramolecular Organogels Derived from Urea and Bisurea Derivatives of Dehydroabietylamine

The gelation ability of diterpenes was investigated by applying aromatic linker steroid strategy. Four new mono (1) and bis-urea (2–4) derivatives of dehydroabietylamine (DAA) (a tricyclic diterpene amine) were synthesized on reaction of respective isocyanates with DAA and characterized through spectroscopic data. Three of these (1, 2, and 4) were obtained as low-molecular-weight organogelators that can form thermally reversible organogels.

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Pd-Catalyzed Cross-Coupling of Acyl Chlorides with In Situ–Generated Alkynylzinc Derivatives for the Synthesis of Ynones

A mild and operationally simple procedure by Pd-catalyzed cross-coupling of acyl chlorides with in situ–generated alkynylzinc derivatives was developed, giving the corresponding ynones in good yields.

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Stereoselective Synthesis of (Z)-1-Benzhydryl-4-cinnamylpiperazines via the Wittig Reaction

A synthetic method of producing (E)- and (Z)-isomers of 1-benzhydryl-4-cinnamylpiperazines in a specific ratio from corresponding benzhydrylpiperazine is described. Of the three compounds synthesized (5a–c), the ratio of E/Z-isomers remained around 15:85. The key intermediates, 1-benzhydryl-4-(2,2-dimethoxyethyl)piperazine derivatives (3a–c), were prepared by nucleophilic substitution reaction of benzhydrylpiperazines (2a–c) with chloroacetaldehyde dimethylacetal in good yield (up to 88%). Hydrolysis of 3a–c gave the corresponding aldehydes 4a–c, which when subjected to the Wittig reaction followed by column purification to afford 1a–c (E-isomers) and 6a–c (Z-isomers) in pure form. The isolated compounds were characterized by NMR and mass spectral analysis.

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An Expedient Approach for the Synthesis of 1-Alkyl-4-propionylpyrrolidin-2-ones

A simple and useful tandem addition–cyclization reaction of primary amines on a prepared α-functionalized propylvinyl ketone 3 in methanol at reflux is a promising route for the synthesis of a new family of 1-alkyl-4-propionylpyrrolidin-2-ones 4.

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Synthesis of Bisindolylindeno[1,2-b]quinoxaline and Bisindolylindeno[3,4-b]pyrazine with Poly(N,N′-dibromo-N-ethylnaphthyl-2,7-disulfonamide)

Poly(N,N′-dibromo-N-ethylnaphthyl-2,7-disulfonamide) (PBNS) as novel reagent was synthesized. Bisindolylindeno[1,2-b]quinoxaline and bisindolylindeno[3,4-b]pyrazine derivatives were synthesized in a simple and efficient method from the three-component condensation reaction of indole, indane-1,2,3-trione, and diamine aromatic compounds by PBNS under solvent-free conditions at 80 °C in good to excellent yields, short reaction times, and a simple procedure for new derivatives.

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Efficient Synthesis of 1,3,5-Benzotriazocines from Tetrachloro-2-aza-1,3-dienes

Easily accessible 1-aryl-2-aza-1,3-butadienes undergo a regioselective cyclocondensation with 2-(aminomethyl)aniline, giving rise to 1,3,5-benzotriazocines in good yields. The structure of the title compounds was proved with the aid of ¹H and ¹³C NMR spectra and, in one case, single-crystal x-ray analysis.

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One-Pot Synthesis of Novel 2-(Thiazol-2-yl)-4,5-dihydropyridazin-3(2H)-one Derivatives Catalyzed by Activated KSF

A series of 2-(thiazol-2-yl)-4,5-dihydropyridazin-3(2H)-one derivatives were synthesized by one-pot multicomponent cyclocondensation of ketoacid, thiosemicarbazide, and phenacyl bromide using catalytical amount of KSF in EtOH under reflux. The straightforward synthesis, presence of two important class of heterocyclic rings in the individual molecule, easy workup of the products, rapid reaction, mild conditions, and good to excellent yields are notable features of this protocol.

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Synthesis of 2-Tert-butylimino-3-hepta-O-benzoyl-β-D-lactosylimino-4-S-benzyl-6-arylimino-2,3-dihydro-1,3,5-thiadiazines

A new series of synthesis of 2-tert-butylimino-3-hepta-O-benzoyl-β-D-lactosylimino-4-S-benzyl-6-arylimino-2,3-dihydro-1,3,5-thiadiazines (hydrochloride) were synthesized by the interaction of 1-aryl-5-hepta-O-benzoyl-β-D-lactosyl-2-S-benzyl-2,4-isodithiobiurets with tert-butyl isocyanodichloride. The identities of these newly synthesized N-lactosides have been established on the basis of usual chemical transformations and infrared, ¹H NMR, and mass spectral analysis.

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Synthesis of 3-(2-(4,5-Dihydro-3,5-diphenylpyrazol-1-yl)thiazol-4-yl)-2H-chromen-2-one Derivatives via Multicomponent Approach

An efficient synthesis of 3-(2-(4,5-dihydro-3,5-diphenylpyrazol-1-yl)thiazol-4-yl)-2H-chromen-2-one derivatives by a simple, atom-economical, and multicomponent reaction of chalcones, thiosemicarbazide, and 3-(2-bromoacetyl) coumarins in the presence of aqueous sodium hydroxide in refluxing ethanol is reported. The structures of newly prepared compounds have been confirmed by their analytical and spectral (IR, ¹HNMR, ¹³CNMR and mass) data.

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Ferrocenoyl Benzotriazole,IV: Microwave-Assisted Synthesis of Novel 1,1′-Bis-ferrocenamides

An easily applicable microwave-assisted novel 1,1′-bis-ferrocenoylbenzotriazole-mediated synthesis of novel derivatives for 1,1′-bis-ferrocenamides was applied. This is a cheap, easy, and green method because of microwave irradiation and recovery of benzotriazole.

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Synthesis and Structure of a Novel Alkynyl-Containing Disulfide Compound as Cathode Materials for Secondary Lithium Batteries

A novel alkynyl-containing disulfide compound, 5,8-dihydro-1H,4H-2,3,6,7-tetrathia-anthracen (TMSEDTTA), was synthesized. The structures of the target compound and the intermediates have been identified by ¹H NMR, ¹³C NMR, mass spectrometry, Fourier-transform infrared, Raman spectra, x-ray photoelectron spectroscopy, and elemental analysis. In addition, the structure of (Z)-(1,2-dibromo-2-(2,3,5,6-tetrakis(bromomethyl)phenyl)vinyl)trimethylsilane (5) was determined by single x-ray analysis.

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Vilsmeier Reagent: An Efficient Reagent for the Transformation of 2-Aminobenzamides into Quinazolin-4(3H)-one Derivatives

Clean and easy preparation of quinazolin-4(3H)-one derivatives using 2-aminobenzamides and Vilsmeier reagent is described. 2-Aminobenzamides were converted into the corresponding quinazolinones under mild and efficient conditions, in good yields without undesirable by-products.

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Synthesis of an Advanced Precursor of Demethoxyviridin

The synthesis of a potential precursor 3 to demethoxyviridin (1b) is described. The centerpiece of this strategy was the conversion of the previously described dibromoolefin 6 to the masked alkyne β-hydroxyaldehyde 5 in a single step. Further elaboration then produced the alkyne oxazole 4, which on thermolysis, followed by in situ tautomerization and silylation, led directly to 3.

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Novel,Recyclable, and Thermally Stable Task-Specific Ionic Liquid (TBA Acetate) Medium/Catalyst for the Synthesis of Indolylidinecyclic-1,3- and -1,4-diketones

A simple and efficient synthesis of indolylidinethiazolidnediones (3) and indolylidinecyclic-1,3-diketones (5) has been developed by reaction of indole-3-aldehyde (1) with thiazolidinedione (2) or cyclic-1,3-diketones (4) using tetra butyl ammonium acetate (TBAA) melt as novel, cost-effective, and recyclable ionic liquid under solvent-free green conditions at 100 °C for 15–20 min without additional use of catalyst.

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