Reactions Between 4-Hydroxycoumarins or 4-Hydroxy-1-Methylquinolinone and Dmad in the Presence of Phosphites. Synthesis of (Chromen-3-YL)- and (Quinolin-3-YL)-(Dialkoxyphosphoryl)Succinates

Abstract

Dimethyl (chromen-3-yl)-(dialkoxyphosphoryl)succinates are prepared from the reaction of 4-hydroxycoumarin with DMAD and P(OR)₃. 4-Hydroxy-1-methylquinolinone reacts with DMAD and P(OEt)₃ to give dimethyl (quinoline-3-yl)-(diethoxyphosphoryl)-succinate.

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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.

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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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Investigation on the Ring-Opening Reactions of 3-(1H-1,2,4-Triazol-1-yl)1,5-benzothiazepines with Arylonitrile Oxides

Abstract

Novel ring opening compounds, (Z)-2-((Z)-((E)-1,3-diaryl-2-(1H-1,2,4-triazol-1-yl)allylidene)amino)aryl N-hydroxybenzimidothioates 4a–r, were obtained from the reaction of 2,4-diaryl-3-(1H-1,2,4-triazol-1-yl)-2,5-dihydro-1,5-benzothiazepines 3a–f and arylonitrile oxides. The structure of these products has been elucidated by spectroscopic analysis and, in one case, X-ray crystallographic analysis. According to the result, it was presumed that this reaction did not proceeded through 1,3-dipolar cycloaddition reaction.

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Synthesis and Characterization of Novel Quinazoline-Substituted 1,3,4-Thiadiazolium-5-thiolates

Abstract

Novel 3-[4-(6-bromo-4-oxo-2-phenylquinazolin-3(4H)-yl)benzoyl]-2-substituted-1,3,4-thiazolium-5-thiolate 7(a–j) and 3-{4-[(6-bromo-2-phenylquinazolin-4-yl)amino] benzoyl}-2-substituted-1,3,4-thiadiazolium-5-thiolate 12(a–j) were synthesized from 6-bromo-2-phenyl-4H-3,1-benzoxazin-4-one (1). The structures of the newly synthesized compounds were confirmed by spectral data and elemental analysis.

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Synthesis and Spectral Characterization of Some Novel Thiazolyl-Pyrazoline Derivatives Containing 1,2,3-Triazole Moiety

Abstract

A series of novel 3-aryl-5-(2-aryl-1,2,3-triazol-4-yl)-1-(4-aryl-2-thiazoyl)-pyrazolines 6a–6r were synthesized using 2-aryl-4-formyl-1,2,3-triazoles 1a,b as the starting materials. Thus, reacting 1a,b with 1-arylethanones 2a–2c gave 1-aryl-3-(2-aryl-1,2,3-triazol-4-yl)-2-propen-1-ones 3a–3f. The reaction of the latter with thiosemicarbazide afforded 3-aryl-5-(2-aryl-1,2,3-triazol-4-yl)-1-thiocarbamoyl-pyrazolines 4a–4f, which condensed with 2-bromo-1-arylethanones 5a–5c to afford the target compounds 6a–6r. The chemical structures of the compounds were verified by means of their IR, ¹H NMR, ESI-MS spectroscopic data, and elemental analysis.

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Synthesis and anti-diabetic activity evaluation of phosphonates containing thiazolidinedione moiety

Abstract

A sequence of substituted phosphonates containing the thiazolidinedione moiety was synthesized with good yields. The structures of all the synthesized compounds were confirmed by NMR (³¹P, ¹H and ¹³C) and IR spectroscopy, mass spectrometry and C, H, N elemental analyses. In silico molecular docking study was also carried out to evaluate their interaction and binding modes on ligands against human PPAR γ protein for their anti-diabetic activity. From the docking results, it was determined that the compounds (Z)-dimethyl 5-(3-nitrobenzylidene)?2,4-dioxothiazolidin-3-ylphosphonate (7a), (Z)-dimethyl 5-(3-chloro-4-fluorobenzylidene)?2,4-dioxothiazolidin-3-ylphosphonate (7f), (Z)-dimethyl 5-(2,4-dichlorobenzylidene)?2,4-dioxothiazolidin-3-ylphosphonate (7e) and (Z)-dimethyl 5-((5-methoxypyridin-2-yl)methylene)?2,4-dioxothiazolidin-3-ylphosphonate (7j) have shown better binding energies (?7.8, ?7.6, ?7.5 and ?7.6 Kcal/mol) with the target gene, PPAR γ than the reference drug, Rosiglitazone (?7.4 Kcal/mol). In vitro anti-diabetic activity of the title compounds was also screened by standard α-amylase inhibition assay. Some of the tested compounds proved to possess promising activity when compared with the reference drug.     

Synthesis and Antimicrobial Activity of Some New 5-(3-Chloro-1-Benzothiophen-2-YL)-1,3,4-Oxadiazole-2-Thiol and Their Derivatives

Abstract

3-Chloro-1-benzothiophene-2-carbonylchloride 1 was made to reacts with hydrazine hydrate afforded 3-chloro-1-benothiophene-2-carbohydrazide 2 in good yield. 5-(3-chloro-1-benzothiophen-2-yl)-1,3,4-oxadiazole-2-thiol 4 was synthesized from 3-chloro-1-benzothiophene-2-carbohydrazide 2. Mannich bases, alkyl halide, and acid chlorides derivatives were then prepared. Compound 4 on condensation with chloroacetone in the presence of NaOH as base and ethanol as solvent gave 1-{[5-(3-chloro-1-benzo[b]thiophen-2-yl)-1,3,4-oxadiazol-2-yl]sulfanyl}propan-2-on 6. Condensation of compound 6 with various aromatic aldehydes afforded a series of chalcones 7a–h. The structures of all the synthesized compounds were confirmed by spectral data and have been screened for antibacterial activity.

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Reaction of 1-Aryl-1H-1,2,3-Triazole-4-Carbonyl Chlorides/Isothiocyanates with 3-Amino-5-Methylisoxazole

Abstract

1-Aryl-1H-1,2,3-triazole-4-carbonyl chlorides were selected as starting materials for the Boulton–Katritzky rearrangement. When 3-amino-5-methylisoxazole was acylated by 1-aryl-1H-1,2,3-triazole-4-carbonyl chlorides, 1-aryl-5-methyl-N-(5-methylisoxazol-3-yl)-1H-1,2,3-triazole-4-carboxamides 5 were obtained and no further rearrangement occurred. On the other hand, when 1-aryl-1H-1,2,3-triazole-4-carbonyl chlorides were first converted into isothiocyanates by the reaction with KSCN and then were allowed to react with 3-amino-5-methylisoxazole 4 in one pot, intermediate thioureas were formed and spontaneously transformed in statu nascendi into 1,2,4-thiadiazole derivatives 6.

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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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Synthesis and Herbicidal Activity of O,O-Dialkyl(phenyl)-N-{1-[(6-chloropyridin-3-yl)methyl]-4-cyano-1H-1,2,3-triazol-5-yl}-1-amino-1-substitutedbenzyl-phosphonates

Abstract

A series of novel α-amino phosphonate derivatives containing both pyridine and 1,2,3-triazole moieties 4 were synthesized via a multi-step reaction. First, the condensation of 5-amino-1-[(6-chloropyridin-3-yl) methyl]-4-cyano-1H-1,2,3-triazole with various aromatic aldehydes in the presence of magnesium perchlorate afforded imines 3 in moderate yields; second, imines 3 reacted with dialkyl phosphites or triphenyl phosphite to give the title compounds 4 in moderate to good yields. Their structures were elucidated by spectroscopic data (IR, ¹H NMR, ³¹P NMR, ESI-MS) and elemental analysis. The preliminary bioassay (in vitro) indicated that some of the title compounds 4 possessed moderate herbicidal activities against dicotyledonous plants (Brassica campestris L) at a concentration of 100 mg/L. However, compounds 4 did not exhibit herbicidal activities against Brassica campestris L at a concentration of 10 mg/L.

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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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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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Synthesis and Characterization of [1,2,4,6]Thiatriazino[2,3-a][1,3]benzimidazol-1(2H)-one and [1,3,5]Thiadiazino[3,4-a][1,3]benzimidazol-2-imine

Abstract

The reaction of thionyl chloride with amidines 2, derived from N-benzimidazol-2-yl imidates 1, leads to [1,2,4,6]thiatriazino[2,3-a][1,3]benzimidazol-1(2H)-one 3 in good yields. [1,3,5]Thiadiazino[3,4-a][1,3]benzimidazol-2-imine 4 was prepared by condensation of NaSCN with benzimidazol-2-yl imidate 1. The isolated compounds 3 and 4 were identified by spectroscopic methods including IR, ¹H NMR, and ¹³C NMR as well as elemental analyses and MS of 3d and 4b.

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Synthesis and Biological Evaluation of Novel Phosphonates Derivatives of As Potential Antitumor Agents

Abstract

A series of dialkyl [2-(4,6-dimethoxypyrimidin-2-yloxy)benzamido](aryl) methylphosphonates derivatives were designed and synthesized. All the new compounds were identified by elemental analysis, IR, ¹H NMR, ³¹P NMR, and MS. Their antitumor activity against KB and CNE1 cells was examined. Some of the compounds showed potential antitumor activity, which provided some hints for further study of structure modification. In particular, the compounds 6i and 6j displayed more potent cytotoxic activities against KB in comparison with 5-FU.

[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]

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