Acid-binding Agent Research Articles

Study in the synthesis and crystal structure of the potentially genotoxic impurity E of Avanafil

In the classical route of synthesizing of avanafil, the last step of the reaction uses EDCI and HOBT as an acid and amine binding agent. HOBT may contain residues of hydrazine, and potential mutagenic impurities containing acylhydrazide structures may be formed. The intermediate product (M6) of avanafil was synthesized by 6 steps using diethyl ethoxylmethylmalonate and S-methyl isothiourea semisulfide as starting materials. The potentially genotoxic impurity E (Imp-E) of avanafil was given by the reaction of M6 and hydrazine sulfate acid amine, yield of 20%. The single crystal of Imp-E was cultivated by solvent volatilization method, and its structure was analyzed by high resolution mass spectrometry (HRMS) and nuclear magnetic resonance spectroscopy (NMR). The Flack parameter of Imp-E was -0.03(3) by X-ray single crystal diffraction analysis, and the absolute configuration of Imp-E was determined as S configuration. The intramolecular / intermolecular hydrogen bonds of Imp-E make the molecules maintain a stable arrangement in space.

An advanced hybrid fibrous separator by in-situ confining growth method for high performance lithium-ion batteries

Separators with superior electrolyte property and thermal stability are in urgent need for high-performance lithium-ion batteries. This work designs a rational confining polymerization method to fabricate an advanced composite separator, in which poly(cyclotriphosphazene-co-4,4-sulfonyldiphenol) microspheres (PZSMS) grow directly in poly(vinylidene fluoride) (PVDF) fibrous membrane. To regulate the size and distribution of PZSMS, triethylamine vapor as acid-binding agent is introduced into PVDF membrane separately from the polymeric monomers. This confining strategy promotes the formation of hybrid fibers with PVDF cores and PZSMS shells. The separator comprised of core-shell structured fibers presents better properties than commercial separators. For example, the optimized separator has higher electrolyte uptake of 433%, ionic conductivity of 1.47 mS/cm, mechanical strength of 26.8 MPa, and better interfacial compatibility. Meanwhile, the heat resistance of the robust PZSMS shell endows this separator with lower thermal shrinkage of 1.8% at 150 °C for 0.5 h and preferable flame-retardant property. In LiCoO2/graphite cells, the optimized separator exhibits a satisfactory capacity retention of 76% at 8.0 C compared with that at 0.5 C and preferable cycling stability with a capacity retention of 97% after 200 cycles. Thus, this PVDF fibrous membrane modified with PZSMS can be a promising candidate for lithium-ion batteries.

Design, synthesis and anti-hypoxia activity of HPN derivatives containing lipophilic long chains.

To design and synthesize long-chain substituted 2-[(4'-hydroxyethoxy) phenyl]-4,4,5,5-tetramethyl-2-imidazoline-1-oxyl 3-oxide (HPN) derivatives with enhanced anti-hypoxic activity. HPN derivatives 1, 3, 5 containing lipophilic long chains were synthesized via the alkylation of HPN with 6-bromohexan-1-ol, ethyl 6-bromohexanoate or 6-bromohexane, respectively using acetonitrile as the solvent and K 2CO 3 as the acid-binding agent at 60 ℃. Derivative 2 was synthesized via hydrolysis reactions of derivative 1 in the NaOH/CH 3OH/H 2O system. Using dichloromethane as the solvent and N, N'-diisopropylcarbodiimide as the dehydrating agent, HPN underwent esterification with hexanoic acid to obtain derivative 4. The structures of derivatives 1-5 were characterized by infrared spectroscopy, electron paramagnetic resonance and high resolution mass spectrometry. The purities of derivatives were detected by high performance liquid chromatography, and the lipid solubilities of derivatives were evaluated by calculating the oil-water partition coefficients (log P). Anti-hypoxia activities of HPN and its long-chain lipophilic derivatives 1-5 were evaluated using normobaric hypoxia test and acute decompression hypoxia test. The structures of the derivatives were confirmed by infrared spectroscopy, electron paramagnetic resonance and high resolution mass spectroscopy. The yields of target derivatives were all above 92%, and the purities were all above 96%. The log P values of derivatives 1-5 were 2.78, 2.00, 2.04, 2.88 and 3.10, which were higher than that of HPN (0.97). Derivatives 1-5 significantly prolonged the survival time of mice at the dose of 0.3 mmol/kg in normobaric hypoxic test and reduced the mortality rate of acute decompression hypoxic mice to 60%, 70%, 60%, 70% and 40%, respectively. The synthesis of derivatives 1-5 is convenient, and the yield is high. The synthesized derivatives especially derivative 5 show anti-hypoxic activity similar to or better than HPN at lower doses.

Structural and electrochemical investigations of new mononuclear nickel(II) dithiolate complexes bearing a pendant amine

To further develop the biomimetic chemistry of [FeFe]- and [NiFe]-hydrogenases for the catalytic reduction of protons to hydrogen (H2), two new mononuclear Ni(II) ethanedithiolate complexes [{(Ph2PCH2)2NR}Ni(SCH2CH2S)] (R = tert-butyl (Bu t ), 1 and n-butyl (Bu n ), 2) with pendant amine-containing diphosphines were synthesized in moderate yields from the treatments of mononickel dichlorides [{(Ph2PCH2)2NR}NiCl2] with ethanedithiol (HSCH2CH2SH) with triethylamine (Et3N) as an acid-binding agent at room temperature. The as-prepared complexes 1 and 2 have been fully characterized by means of elemental analysis, nuclear magnetic resonance (NMR) spectrum, and X-ray crystallography. Further, the electrochemical properties of 1 and 2 are investigated in the absence or presence of acetic acid (HOAc) by using cyclic voltammetry (CV), suggesting that they can be considered as the active electrocatalysts for proton reduction to H2.

Mononuclear nickel(II) dithiolate complexes with chelating diphosphines: Insight into protonation and electrochemical proton reduction

Inspired by the metal active sites of [FeFe]- and [NiFe]‑hydrogenases, a series of mononuclear Ni(II) ethanedithiolate complexes [{(Ph2PCH2)2×}Ni(SCH2CH2S)] (X = NCH2C5H4N-p (2a), NCH2C6H5 (2b), NCH2CHMe2 (2c), and CH2 (2d)) with chelating diphosphines were readily synthesized through the room-temperature treatments of mononuclear Ni(II) dichlorides [{(Ph2PCH2)2×}NiCl2] (1a-1d) with ethanedithiol (HSCH2CH2SH) in the presence of triethylamine (Et3N) as acid-binding agent. All the as-prepared complexes 1a-1d and 2a-2d are fully characterized through elemental analysis, nuclear magnetic resonance (NMR) spectrum, and by X-ray crystallography for 1b, 2a-2d. To further explore proton-trapping behaviors of this type of mononuclear Ni(II) complexes for catalytic hydrogen (H2) evolution, the protonation and electrochemical proton reduction of 2a-2c with aminodiphosphines (labeled PCNCP = (Ph2PCH2)2NR) and reference analogue 2d with nitrogen-free diphosphine (dppp = (Ph2PCH2)2CH2) are studied and compared under trifluoroacetic acid (TFA) as a proton source. Interestingly, the treatments of 2a-2d with excess TFA resulted in the unexpected formation of dinuclear Ni(II)-Ni(II) dication complexes [{(Ph2PCH2)2×}2Ni2(μ-SCH2CH2S)](CF3CO2)2 (3a-3d) and mononuclear Ni(II) N-protonated complexes [{(Ph2PCH2)2N(H)R}Ni(SCH2CH2S)](CF3CO2) (4a-4c), which has been well supported by high-resolution electrospray ionization mass spectroscopy (HRESI-MS), NMR (31P, 1H) as well as fourier transform infrared spectroscopy (FT-IR) techniques, and especially by X-ray crystallography for 3d. Additionally, the electrochemical properties of 2a-2d are investigated in the absence and presence of strong acid (TFA) by using cyclic voltammetry (CV), showing that the complete protonation of 2a-2d gave rise to dinuclear Ni2S2 species 3a-3d for electrocatalytic proton reduction to H2.

A one-pot synthesis of 2-aminothiazoles via the coupling of ketones and thiourea using I2/dimethyl sulfoxide as a catalytic oxidative system

A series of 2-aminothiazoles is prepared in moderate-to-good yields by the direct coupling of ketones and thiourea using I2/dimethyl sulfoxide as a catalytic oxidative system. This method avoids the preparation of lachrymatory and toxic α-haloketones and the use of an acid-binding agent, thus providing a more convenient approach to 2-aminothiazoles compared to the Hantzsch reaction.

Novel P/N/Si/S-containing Mononickel Complex as a Metal-based Intumescent Flame Retardant for Cotton Fabrics

A new P/N/Si/S-containing mononickel complex NiS, which can be regarded as a rare type of the metal-based intumescent flame retardant, has been prepared through the condensation reaction of precursor NiCl with 1, 2-ethanedithiol in the presence of Methylamine as acid-binding agent. Its molecular structure is well characterized by elemental analysis, infrared (IR) and nuclear magnetic resonance (NMR) spectroscopies. The target flame retardant NiS has been successfully applied to cotton fabrics through a pad-dry-cure method. Thermal degradation properties of neat and treated cotton fabrics with 10.7 wt% NiS are studied by thermogravimetric analysis (TGA). Flammability behaviors of neat and treated cotton with 10.7 wt% NiS are evaluated using vertical burning test, limiting oxygen index (LOI) and microscale combustion calorimeter (MCC). Meanwhile, to further investigate the flame retardancy of NiS for cotton fabrics, the char layers of neat and treated samples after combustion are analyzed by SEM image and Raman spectroscopy. As a result, the improved thermal and flammability performance for cotton fabrics by introduction of NiS might be due to the metal-assisted catalytic charring effect of NiS on the formation of the compact char layer and the release of the flammable gas.

Microwave-assisted efficient synthesis of 3-substituted bis-isoxazole ether bearing 2-chloro-3-pyridyl via 1,3-dipolar cycloaddition.

An efficient strategy for synthesizing of 3-substituted bis-isoxazole ether bearing 2-chloro-3-pyridyl under microwave radiation was reported. The reactive regioselectivity was improved by changing mainly the solvent and acid-binding agent. 3-(2-Chloropyridin-3-yl)-5-(((3-substituted phenyl isoxazol-5-yl)methoxy)methyl)isoxazoles were synthesized in 31-92% yields and were characterized by FT-IR, HRMS, 1H and 13C NMR spectroscopy. The single crystal of 3-(2-chloropyridin-3-yl)-5-(((3-(p-tolyl)isoxazol-5-yl)methoxy)methyl)isoxazole was obtained, and the structure of compound has also been determined by X-ray diffraction technique. Weak intra- and intermolecular C-H∙∙∙O interactions and a C-H∙∙∙π interaction link molecules into a three-dimensional network. The results showed that the synthesized compounds belonged to triclinic system, and their regioselectivity depended on the solvent and acid-binding agent. The merits of this method include the environmentally friendly, efficient, simple operation, and higher regional selectivity. An efficient synthesis of 3-substituted bis-isoxazole ethers was developed via 1,3-dipolar cycloaddition reaction starting from 3-substituted phenyl-5-((prop-2-yn-1-yloxy))methyl)isoxazoles and (Z)-2-chloro-N-hydroxynicotinimidoyl chloride using NaHCO3 as an acid-binding agent in THF solvent-dissolved trace water under catalyst-free microwave-assisted conditions.

The introduction of benzimidazole and ether moieties into poly(p-phenylene terephthalamide): effects on its microstructure, interactions and properties.

Co-poly(p-phenylene terephthalamide) (co-PPTA) fibers containing 4,4′-oxidianiline (4,4′-ODA) and 2-(4-aminophenyl)-5-aminobenzimidazole (BIA) in terephthaloyl chloride (TPC) and p-phenylene diamine (p-PDA) were prepared via a wet spinning method, followed by water washing and drawing at a high temperature. With the addition of a new acid-binding agent, imidazole, the solution prepared by low-temperature polycondensation had suitable viscosity for spinning. Herein, the properties of six co-PPTA fibers with different contents of BIA and 4,4′-ODA segments were studied. The mechanical properties of the co-PPTA fibers were improved with the addition of BIA and ODA; they reached the optimum tensile strength of 2.45 GPa at a p-PDA/ODA/BIA molar ratio of 2/4/4, which showed a higher degree of orientation and the highest crystallinity, and the strength further increased on increasing the thermal drawing ratio. X-ray diffraction indicated that the fibers exhibited highly ordered structures, while two-dimensional wide angle X-ray diffraction showed that molecular packing regions with highly oriented structures were formed. In addition, the co-PPTA fibers exhibited excellent thermal stability when the 5% weight loss temperature was above 492 °C under nitrogen, and glass transition occurred at about 290 °C.

Preparation and evaluation of amine terminated polyether shale inhibitor for water-based drilling fluid

Facing the problems of shale hydration, swelling and borehole wall instability in shale gas drilling, a new type of amine terminated polyether (ATPE) shale inhibitor used in water-based drilling fluid is successfully synthesized through the method of leaving group. Using the yield of ATPE as index, orthogonal experiments are designed to determine the optimal reaction conditions. When the mole ratio of polyethylene glycol tosylate (PEG-OTs)/ethylenediamine is 1/3.6, mole ratio of PEG-OTs/triethylamine (acid binding agent) is 1/4, reaction time is 3.5 h and reaction temperature is 60 °C, the yield of ATPE is 91.12%. The structure and molecular weight of polyethylene glycol (PEG-400, a kind of oligomer), PEG-OTs and ATPE are characterized by Fourier transform infrared spectroscopy, nuclear magnetic resonance hydrogen spectroscopy (H1-NMR) and time of flight mass spectrometer. The characterization results show that the ATPE has a reasonable molecular weight, and the both hydroxyls of PEG-400 have been replaced by ethylenediamine. The inhibition property of ATPE, potassium chloride (KCl), potassium formate (KCOOH), methane-siliconic acid (FMS-1) and polymeric alcohol (JLX-B) are comparatively evaluated through shale rolling dispersion experiment, linear expansion experiment and laser particle size test. The results show that the ATPE has a better shale inhibition property than traditional inhibitors. The drilling fluid system performance evaluation results show that the system has good engineering application value with excellent rheological property, low fluid loss and good shale inhibition property, which guarantee the well-bore stability in shale gas drilling.

Esterification of Cochineal Carmine Used for Dyeing Cationic Modified Cotton with High Color Fastness

In order to reduce the electronic cloud density for higher color fastness, ester groups were introduced into cochineal carmine matrix structure. The optimum esterification conditions were selected by varying the level of acid-binding agent, the reaction temperature, the reaction time, and the amount of acetylation reagent. The structure and properties of esterified cochineal carmine was characterized by UV-vis spectroscopy, FT-IR spectrometry and metallographic microscopy. The build-up property, dyeability, light fastness, perspiration and rubbing fastness of cochineal carmine before and after esterification on cationic modified cotton were investigated. The results show that the optimum esterification condition is treating 1.0 g cochineal carmine with 50 mL acetic anhydride and 4.0 g anhydrous sodium acetate at 80°C for 2.0 hours. The acid perspiration fastness and wet rubbing fastness of the resulting dyed samples were increased by one grade. The perspiration fastness to alkalis and the light fastness were improved by one-half grade.

Continuous synthesis of ginkgolide B derivatives in a micro-flow system

In this study, etherification process of ginkgolide B in a micro-flow system was investigated. With calcium carbonate as an acid-binding agent, the optimal result was obtained in such conditions: residence time 3min, temperature 85°C, molar ratio of ginkgolide B to dimethylamino ethyl chloride hydrochloride 1:2, molar ratio of ginkgolide B to potassium iodide 1:0.2, and molar ratio of ginkgolide B to calcium carbonate 1:2.5. Meanwhile, this novel process in MFS could proceed well for the etherification reaction between ginkgolide B and other halides, to afford the target products in moderate yields. Besides, salification reaction was conducted in a valve assisted micromixer by reacting dimethylaminoethyl ginkgolide B with methane sulfonic acid. Compared with conventional drugs, enhanced bioavailability was obtained when nano-scale drugs were dosed.

A Facile Synthesis of 2-(Benzofuran-2-yl)-6-chloroquinoline-3-carboxylic Acid Derivatives

A facile synthesis of 2-(benzo(naphtho)furan-2-yl)-6-chloroquinoline-3-carboxylic acid derivatives (3a~p) has been described, involving ultrasound-assisted three-step one-pot reaction of ethyl 6-chloro-2-(chloromethyl)quinoline3-carboxylate (1) with corresponding salicylaldehydes (2a ~ 2i), 1-(2-hydroxyphenyl)ethanones (2j ~ 2o) or 2-hydroxy-1-naphthaldehyde (2p) in the presence of K2CO3 as acid-binding agent and PEG-400 as phase transfer catalyst in refluxing MeCN. The synthesized compounds were new, and their structures had been determined by IR, H NMR, C NMR and HRMS.

Homogeneous Acylation and Regioselectivity of Cellulose with 2-Chloro-2-Phenylacetyl Chloride in Ionic Liquid

A cellulose acylate, cellulose-CPAC, was prepared homogeneously in the ionic liquid 1-butyl-3-methyl chloride imidazole ([Bmim]Cl) from cotton dissolving pulp. The pulp was first solubilized in the solvent system [Bmim]Cl/N,N-dimethyl formamide (DMF), and then reacted with 2-chloro-2-phenylacetyl chloride (CPAC) in the presence of an acid-binding agent. The effects of functional conditions including the molar ratio of CPAC/anhydroglucose unit (AGU), reaction time, reaction temperature, kind of acid-binding agent, and cellulose concentration on the degree of substitution (DS) were studied. The reactivities of the three hydroxyl groups in the homogeneous acylation of cellulose with CPAC were also investigated. The results showed that in homogeneous reaction medium, although all the C-6, C-3, and C-2 positions within the cellulose AGU could be substituted by CPAC, the reaction was quite selective for the C-6 OH. The successful synthesis of the cellulose-CPAC was confirmed by FT-IR, 1H NMR, 13C NMR, XRD, and STA. Furthermore, the acylation of cellulose with CPAC decreased the thermal stability of cellulose.

Synthesis of a novel triazine flame retardant containing sulfur and its application to cotton fabrics

A novel triazine flame retardant (FR) has been successfully synthesized by the reaction of cyanuric chloride with sodium sulfanilate followed by diethanol amine. Its structure has been fully characterized by IR and 1H NMR spectroscopy. The effects of reaction solvent, acid-binding agent, reaction temperature, and molar ratio of starting materials on the yield of FR were investigated in detail. Experiments showed that when the molar ratio of intermediate I to diethanol amine is 1 to 1.2 in the presence of sodium carbonate as acid-binding agent in acetone-water at 45 °C, the yield of the obtained FR reaches 81.4%. Thermogravimetry (TG) test indicated that the FR has good thermostability and char-forming ability. In addition, the flame retardancy and thermal behavior of the cotton fabrics treated with FR were studied by limiting oxygen index (LOI), vertical flammability test, and thermogravimetry (TG) to evaluate the flameretardant performance of the target FR. These results demonstrated that the flame retardancy and thermal stability of the cotton fabrics treated with FR were clearly improved.

Study on Synthesis of Cyclotriphosphazene Containing Aminopropylsilicone Functional Group as Flame Retardant

A novel non-halogen flame retardant APESP, cyclotriphosphazene containing six aminopropyltriethoxysilicone functional groups N3P3[NH(CH2)3Si(OCH2CH3)3]6, was synthesized by menas of SN2 nucleophilic substitution reaction, using hexachlorocyclotriphosphazene(HCCP) and 3-aminopropyltriethoxy-silane (KH550) as material. Firstly the industrial grade HCCP was purified through recrystallization and sublimation. Then the reaction process was investigated to prompt the yield, and the optimum reaction conditions were as follows: triethylamine as acid-binding agent, tetrahydrofuran as solvent, HCCP/KH550/triethylamine molar ratio 1:7.2:7.2, dripping time: 1 hour, temperature: 67°C and reaction time: 20h. Maximum APESP yield reached 94.3%. The chemical structure and purity was characterized by element analysis, Fourier-transformed infrared spectroscopy (FTIR), mass spectrum, gel permeation chromatography (GPC) and nuclear magnetic resonance (NMR) analysis. The results showed that the structure of synthesized product is consistent with the theoretical structure, in which the chlorine atoms were completely substituted. The charge distribution calculation of HCCP and KH550 confirmed the reaction mechanism.

Gene expression analysis on the liver of cholestyramine-treated type 2 diabetic model mice

Recent experimental and clinical studies have indicated that bile acid-binding agents are effective not only for treating hypercholesterolemia, but also for type 2 diabetes. To investigate the molecular mechanism underlying the effect of cholestyramine, a bile acid-binding agent, on type 2 diabetes, we examined gene expression of the livers of cholestyramine-treated type 2 diabetic model mice. Type 2 diabetic NSY/Hos mice were fed a high fat diet supplemented with 1% (w/w) cholestyramine for 8 weeks. Cholestyramine treatment prevented the increase in body weight, plasma cholesterol, triglycerides, glucose, insulin levels, and hepatic steatosis. DNA microarray analysis was performed on the liver, which revealed that the genes related to synthesis of cholesterol and its derivatives were increased and the genes regulated by liver X receptors, such as the sterol regulatory element-binding protein 1 gene, were decreased in the group treated with cholestyramine. Expression of the genes related to carbohydrate metabolism was little changed in the cholestyramine group. Furthermore, we performed real-time RT-PCR analysis, which highly correlated with DNA microarray data ( r = 0.957, P < 0.001). This study provides a valuable basis for further research on the biological functions of bile acid-binding agents in models of type 2 diabetes.

Synthesis of 3-Dehydroabietylamino-2-Hydroxypropyl Trimethylammonium Chloride and its Antibacterial Activity

Abstract In the presence of an acid-binding agent loaded on alumina, 3-dehydroabietylamino-2-hydroxypropyl trimethyl ammonium chloride (DHAHPTMA) was synthesized with dehydroabietylamine (DHA) and 3-chloro-2-hydroxypropyl trimethyl ammonium chloride (CTA) as starting material. The structure of DHAHPTMA was characterized by FT-IR and 1H-NMR, and the content of DHAHPTMA in product was determined by Ion Chromatography (IC). The antibacterial activity of DHAHPTMA was evaluated according to its minimum inhibitory concentrations (MICs) against Staphylococcus aureus (S. aureus), Staphylococcus epidermidis (S. epidermidis), gas bacillus, Klebsiella pneumoniae, Escherichia coli (E. coli), Pseusomonas aeruginosa (P. aeruginosa) and Salmonella. Results of IC showed that the mass content of DHAHPTMA in the product was higher than 97%. The experimental results also indicated that the MICs of DHAHPTMA against S. aureus, S. epidermidis and E. coli were lower than that of Bromo-Geramium against theses bacteria.

Drug interactions with colesevelam hydrochloride, a novel, potent lipid-lowering agent.

Colesevelam hydrochloride (colesevelam) is a novel, potent, bile acid-binding agent that has been shown to lower LDL cholesterol a mean of 19% at a dose of 3.8 g/d. We studied the pharmacokinetics of colesevelam coadministered with six drugs: digoxin and warfarin, agents with narrow therapeutic indices; sustained-release verapamil and metoprolol; quinidine, an antiarrhythmic with a narrow therapeutic index; and valproic acid, an antiseizure medication. Six individual studies were single-dose, crossover, with or without a 4.5-g dose of colesevelam. Plasma levels were determined using validated analytical methods. Values for the ratio of ln[AUC(0-t)] with and without colesevelam were 107% for quinidine, 102% for valproic acid, 89% for digoxin, 102% for warfarin, 82% for verapamil, and 112% for metoprolol. Values for the ratio of ln[Cmax] with and without colesevelam were 107% for quinidine, 92% for valproic acid, 96% for digoxin, 99% for warfarin, 69% for verapamil, and 112% for metoprolol. The 90% confidence intervals for these ratios and for values of ln[AUC(0-inf)] that could be determined were within the 80-125% range, with the exception of verapamil. In this study, verapamil had great interindividual variability, with a 28-fold range in Cmax and an 11-fold range in AUC(0-t). In summary, pharmacokinetic studies with colesevelam did not show clinically significant effects on absorption of six other coadministered drugs.

ONE'POT REACTION OF TRIVALENTPHOSPHORUS COMPOUNDS (I)——A NOVEL ONE-STEP REACTION OF ADDITION,REDUCTION AND CYCLIZATION OF SUBSTITUTED β-NITROSTYRENE WITH O,O-DIALKYL PHOSPHITES

In this paper the reaction of substituted β-nitrostyrene with O,O-dialkyl phosphite under cocatalysis of trimethylsilyl chloride (TMS-C1) and triethylamine (or other acidbinding agent) has been first studied and the new cyclization reaction leading to the formation of product Ⅱ, as a new class of derivatives of 1-hydroxyindoles, difficultly accessible or inaccessible with usual methods has been observed. In the related reaction it is surprising that when the Arbuzov rearrangement occurs under mild conditions, the addition, reduction and cyclization as a one-pot reaction take place simultaneously with the formation of products Ⅰ, Ⅱ, Ⅲ. By controlling the reaction conditions the products were formed almost in specificity, and thus the most interesting cyclic products Ⅱ_(a-h) containing phosphorus-carbon bond were obtained. Their structures were confirmed by elemental analysis, IR, ~1H or ~(31)p NMR and MS spectra. The crystal structure of representative compound Ⅱ_h was determined by X-ray diffraction. The influence of molar ratio of reactants, solvents, substituents on benzene ring, acid-binding agents, time and temperature of reaction on the distribution of products Ⅰ, Ⅱ, Ⅲ was quantitatively investigated by the ~(31)P NMR method. The bioactivity remained to be tested.