Highly efficient synthesis of 2,3-dihydroquinazolin-4(1H)-ones catalyzed by heteropoly acids in water

Heteropoly acids efficiently catalyzed the cyclocondensation reaction of anthranilamide with aldehydes in water at ambient temperature and afforded the corresponding 2,3-dihydro-4（1H）-quinazolinones compounds in good to excellent yields.This method provides mild reaction conditions and clean reaction profiles,using a small quantity of catalyst and a simple workup procedure.

Synthesis of some new bis-3,4-dihydropyrimidin-2(1H)-ones by using silica-supported tin chloride and titanium tetrachloride

Silica-supported tin chloride and titanium tetrachloride were prepared by the reaction of tin chloride and titanium tetrachloride with activated silica gel in refluxing toluene.These solid acids have been employed as the catalysts for the synthesis of bisdihydropyrimidin -2(1H)-ones from aromatic dialdehydes,1,3-dicarbonyl compounds and urea at 90℃under solvent-free conditions.

Synthesis and biological evaluation of novel 2,4,5-triaryl-1 H-pyrazol-3(2H)-ones as inhibitors of ALK5

A series of 2,4,5-triaryl substituted 1H-pyrazol-3（2H）-ones,as ALK5 inhibitors,were desigened,synthesized and evaluated in vitro.Most compounds exhibited noticeable ALK5 inhibition activities at 1μmol/L and displayed no significant cytotoxicities at 30μmol/L.

H_3PMo_(12)O_(40) catalyzed three-component one-pot synthesis of 4,6-diarylpyrimidin-2(1H)-ones under solvent-free conditions

4,6-Diarylpyrimidin-2(1H)-one derivatives have been synthesized from three-component one-pot condensation of acetophe-none derivatives,aldehydes and urea in the presence of trimethylsilyl chloride and a catalytic amount of HPMoOunder solvent-free conditions.

One-Pot Three Component Domino Reaction for the Synthesis of Novel Isoxazolo[2,3-<i>c</i>][1,3,5]Thiadiazepin-2-Ones Catalyzed by <i>PTSA</i>—A Green Chemistry Approach

The synthesis of novel isoxazolo[2,3-c][1,3,5]thiadiazepin-2-ones has been achieved in excellent yields by one-pot three-component Domino reaction without the production of toxic waste products by using p-toluene sulfonic acid (PTSA) as a Lewis acid catalyst. PTSA plays a crucial role in the success of the reaction, as well as for increasing reaction rate.

Selenium-catalyzed oxidative carbonylation of 2-aminobenzyl alcohol to give 1,4-dihydro-2H-3,1-benzoxazin-2-one

An efficient,economical,and phosgene-free approach was developed for the preparation of l,4-dihydro-2H-3,l-benzoxazin-2-one from 2-aminobenzyl alcohol.In terms of its key features,this reaction uses the cheap and recyclable non-metal selenium as a catalyst instead of the noble metal palladium;carbon monoxide as a carbonylation agent instead of virulent phosgene or one of its derivatives;and oxygen as an oxidant.The selenium-catalyzed oxidative carbonylation reaction of2-aminobenzyl alcohol proceeded efficiently in a single pot in the presence of triethylamine to afford l,4-dihydro-2H-3,l-benzoxazin-2-one in 87%yield.Furthermore,the selenium catalyst was readily recovered and recycled,affording a product yield of 80%after five cycles.

UPLC-MS/MS法测定槲寄生抗肿瘤成分1,7-bis(4-hydroxyphenyl)-1,4-heptadien-3-one的含量

目的建立超高效液相色谱-串联质谱法(UPLC/MS/MS)测定槲寄生中具有抗肿瘤活性的新化合物1,7-bis(4-hydroxyphenyl)-1,4-heptadien-3-one(BHPHD)的含量,并通过多因素方差分析比较产地与寄主对药材抗肿瘤成分含量的影响。方法以Thermo Hypersil GOLD C18(50 mm×2.1 mm,1.9μm)为分离色谱柱,乙腈-体积分数0.1%甲酸水溶液为流动相,流速0.2 m L·min-1,梯度洗脱,质谱检测器,电喷雾正离子,多反应监测模式,监测离子对m/z 295.09→106.99。结果BHPHD在质量浓度为0.050~2.5 mg·L-1内线性关系良好,精密度、重复性、稳定性试验的RSD均≤3.5%,平均加样回收率(n=9)为97.2%(RSD=1.6%)。结论该方法可满足定量要求。多因素方差分析表明槲寄生中BHPHD的含量受产地影响较大(P<0.01),受寄主影响不大。

An efficient synthesis of 2,2′-arylmethylene bis-(3-hydroxy-5,5-dimethyl-2-cyclohexene-1-one) and 1,8-dioxooctahydroxanthenes using ZnO and ZnO-acetyl chloride

2,2'-Arylmethylene bis(3-hydroxy-5,5-dimethyl-2-cyclohexene-1-one) 4l-s produced from reaction between dimedone with various aldehydes in acetonitrile using ZnO as a catalyst;whereas in the presence of ZnO-acetyl chloride catalysts the reaction is limited to give only 1,8-dioxo-octahydroxanthenes 3a-k in very good yields.

Synthesis and Crystal Structure of 1-(4-Fluorophenyl)-2-hexylthiobenzo[4,5]-furo[3,2-d]-1,2,4-triazolo[1,5-a]pyrimidin-5(1H)-one

The crystal structure of the title compound 1-（4-fluorophenyl） -2-hexylthio-benzo [4,5]furo[3,2-d]-1,2,4-triazolo[1,5-a]pyrimidin-5（1H） -one（C23H21FN4O2S,Mr = 436.5） has been prepared and determined by single-crystal X-ray diffraction. The crystal is of monoclinic,space group P21/n with a = 13.9854（3） ,b = 17.2678（4） ,c = 18.1828（5）A,β = 99.364（2） °,V = 4332.58（18） A^3,Z = 4,Dc = 1.338,F（000） =1824,μ = 0.185 mm^-1,MoKa radiation（λ = 0.71073） ,R = 0.0538 and wR = 0.1162 for 4728 observed reflections with I 〉 2σ（I） . X-ray diffraction analysis reveals the fused rings of benzo[4,5]furo[3,2-d]-1,2,4-triazolo[1,5-a] pyrimidin-5（1H） -one system are nearly coplanar. The crystal packing is mainly stabilized by weak intermolecular C-H···O hydrogen bond and π-π interactions.

Synthesis, Crystal Structure and Fungicidal Activity of (Z)-3,3-Dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one O-2-Chlorobenzyl Oxime Nitrate

The title compound has been synthesized by the reaction of 3,3-dimethyl-1-（1H-1,2,4-triazol-1-yl）butan-2-one oxime with 2-chlorobenzyl chloride, and then treated with 65～68% HNO3. Its crystal structure was determined by single-crystal X-ray diffraction. The crystal belongs to the monoclinic system, space group P21/c with a = 14.5481（8）, b = 9.3351（5）, c = 13.1911（7） , β = 98.9450（10）°, Z = 4, V = 1769.67（17） 3, Mr = 369.81, Dc = 1.388 g/cm3, S = 1.06, μ = 0.247 mm-1, F（000） = 776, the final R = 0.0352 and wR = 0.0960 for 3069 observed reflections （I 2σ（I））. X-ray crystal structure presents the intramolecular N–H…O hydrogen bond. The packing is nearly parallel without π-π stacking interactions between two adjacent phenyl rings and stabilized by Van der Waals force. The preliminary bioassay shows that the title compound possesses fungicidal activity against Gibberella zeae at the dosage of 25 mg/L.

Synthesis and Crystal Structure of Trans-4-[(5-(2,4-Dichlorophenoxy)-3-methyl-1-phenyl-1H-pyrazol-4-yl)methyleneamino]-1,5-dimethyl-2-phenyl-1,2-dihydropyrazol-3-one

The title compound trans-4-[（5-（2,4-dichlorophenoxy）-3-methyl- 1-phenyl-1H-pyrazol-4-yl）methyleneamino]- 1,5-dimethyl-2-phenyl-1,2-dihydropyrazol-3-one 3 （C28H23Cl2N5O2, Mr = 532.41） has been synthesized and its crystal structure was determined by single-crystal X-ray diffraction analysis. It crystallizes in triclinic, space group P1- with a = 8.9438（4）, b = 11.6065（5）, c = 14.2215（6）A, α = 112.566（1）, β = 92.324（2）, γ = 102.91（1）°, V= 1315.65（10） A^3, Z = 2, Dc = 1.344 g/cm^3,μ（MoKa） = 0.282 mm^-1, λ = 0.71073 A, F（000） = 552, the final R = 0.0587 and wR = 0.1578 for 5071 observed reflections （I 〉 2σ（I））. X-ray analysis reveals that the product is a thermodynamically stable trans isomer. Intra- and intermolecular C（ 12）-H（12）…O（1） and C（28）-H（28）...O（1）# 1 hydrogen bonds were observed in the title compound.

The Synthesis of 3-(2'-Hydroxybutyl) isobenzofuran-1 (3H)-one

The synthesis of 3-(2'-hydroxybutyl）isobenzofuran-1(3H)-onel from phthalicanhydride via the intermediate 3-(2'-oxoethyl) isobenzofuran-1(3H)-one 6 was described．

An efficient synthesis of 2,2-bis(1H-indol-3-yl)-2H-acenaphthen-1-one catalyzed by recyclable solid superacid SO_4^(2-)/TiO_2 under grinding condition

An efficient synthesis of symmetrical 2,2-bis（1H-indol-3-yl）-2H-acenaphthen-1-one is achieved via a reaction of acenaphthe-nequinone and indoles catalyzed by solid superacid SO4^2-/TiO2 under solvent-free conditions at room temperature by grinding, which provides an efficient route to the synthesis of symmetrical 2,2-bis（1H-indol-3-yl）-2H-acenaphthen-1-one.This procedure offers several advantages including solvent-free conditions,excellent yields of products,simple work-up as well as reuse of catalysts which makes it a useful and attractive protocol for the synthesis of these compounds.

Synthesis,Crystal Structure and Plant Growth Regulatory Activity of 1-(3-Amino-[1,2,4]triazol-1-yl)-3,3-dimethyl-butan-2-one

The title compound 1-（3-amino-[1,2,4]triazol-1-yl）-3,3-dimethyl-butan-2-one（3） was synthesized by Hofmann-alkylation reaction of 1-chloro-3,3-dimethyl-butan-2-one（1） and ~1H-[1,2,4]triazol-3-ylamine（2） with equal amount of K_2CO_3 as acid acceptor. The structure of compound 3 was characterized by ~1H NMR, 13 C NMR, HRMS and single-crystal X-ray diffraction. The compound crystallizes in the monoclinic system, space group P21/n with a = 5.7227（8）, b = 27.924（4）, c = 6.2282（7） ？, β = 101.892（11）°, V = 973.9（2） ？~3, Z = 4, T = 180.00（10） K, μ（MoKα） = 0.087 mm^（-1）, Dc = 1.243 g/cm^3, 3832 reflections measured（3.648≤θ≤26.022°）, 1916 unique reflections（Rint = 0.0359, Rsigma = 0.0572） used in all calculations. The final R = 0.0557（I 〉 2σ（I）） and w R = 0.1276（all data）. Bioassay showed that 3 displayed excellent activity as plant growth regulator with inducing lateral root formation and enhancing primary root elongation at 0.27 mmol/L（50 ppm） in soybeen（He Feng-50）. Good water solubility was found with 50 mg in 1 m L of water. Therefore, application of 3 in agriculture is more environmentally friendly due to cosolvent-free condition, and results in improved abiotic-stress tolerance by affecting the root growth. And furthermore, it can be used as a precursor to investigate the function of regulating plant root growth.

Synthesis and Crystal Structure of 5,5-Dimethyl-2-(4-chlorophenyl)(3-hydroxy-5,5-dimethyl-2-cyclohexen-1-one-2-yl)methyl-3-(4-methoxyphenylamino)-2-cyclohexene-1-one

The title compound 5,5-dimethyl-2-（4-chlorophenyl）（3-hydroxy-5,5-dimethyl- 2-cyclohexen-1-one-2-yl）methyl-3-（4-methoxyphenylamino）-2-cyclohexen-1-one has been synthesized, and its crystal structure was characterized by X-ray single-crystal diffraction. The crystal belongs to monoclinic, space group P21/c with a = 9.4193（13）, b = 26.915（4）, c= 21.188（3） A, β = 101.906（3）°, V = 5256.2（13） A3, Z = 4, C60H68C12N2O8, Mr =1016.06, Dc = 1.284 g/cm3, F（000） = 2160, λ（MoKα） = 0.71073 A, μ = 0.182 mm^-1, R = 0.0530 and wR = 0.1131 for 4128 observed reflections （1 〉 2α（Ⅰ））. X-ray analysis reveals that there are two independent molecules in the unit and the cyclohexenone rings adopt different conformations. In addition, there are four intramolecular hydrogen bonds in the title molecule.

Synthesis, Crystal Structure and Antibacterial Activity of 1-((2-Chloroquinolin-3-yl)-methyl)-pyridin-2(1H)-one

On the basis of the interesting structures and biological activities exhibited by several heterocyclic systems possessing the pyridone nucleus such as mappcine and camptothecin, we have planed to design the synthesis, crystal studies and antibacterial activity of the new 1-（（2- chloroquinolin-3yl）-methyl）-pyridine-2（1H）-one building block. An X-ray analysis has provided valuable insight into the effect of steric factors on the three-dimensional shape of this compound which serves as a useful advanced intermediate in the synthesis of these biologically active molecules. A multistep synthesis of camptothecin （5） has been designed by retrosynthetic analysis as part of an ongoing program on lead anticancer drug.

Enzymatic Synthesis and Characterization of Novel Polycarbonates Derived from 5-Allyloxy-1, 3-dioxan-2-one and 5, 5-Dimethvl-1.3-dioxan-2-one

Novel polycarbonates from 5-allyloxy-1, 3-dioxan-2-one （ATMC） with 5, 5-dimethyl- 1, 3-dioxan-2-one （DTC） were successfully synthesized for the first time using immobilized porcine pancreas lipase （IPPL） as catalyst. The resulting copolymers were characterized by IR, ^1H NMR, ^13C NMR and GPC. The molecular weight （Mn） of the copolymer with molar feed ratio of 10：90 （ATMC：DTC） was 9300 and the polydispersity was 1.31, while the Mn increased to 14300 and polydispersity of 1.25 with the feed ratio of 50：50. Moreover, the composition of the copolymers agreed well with the monomer feed.

SINGLE LANTHANUM TRIS(N-PHENYLETHYL-3,5-DI-t-BUTYLSALICYLALDIMINATO)S INITIATOR FOR RING-OPENING POLYMERIZATION OF 1,4-DIOXAN-2-ONE IN BULK

A rare earth Schiff base complex:lanthanum tris(N-phenylethyl-3,5-di-t-butylsalicylaldiminato)s [La(OPEBS)_3] was successfully applied as single component initiator for the ring-opening polymerization of 1,4-dioxan-2-one (PDO) in bulk.The influence of reaction conditions,such as polymerization temperature,the molar ratio of the monomer to initiator (M/I) on the monomer conversion and molecular weight of the polymer has been investigated.Poly(1,4-dioxan-2-one) with a viscosity-average molecular weight (My) o...

SYNTHESIS OF 4,6-DISUBSTITUTED 5-THIOXO-1,2,4-TRIAZIN-3-ONE FROM BENZOTHIOFORMANILIDE

A method of synthesis of 4,6-disubstituted 5-thioxo-1,2,4-triazin- 3-ones from benzothioformanilides and semicarbazide is described.And six new compounds were synthesized by this method.

Design and Synthesis of 3,4-Dihydropyrrolo[2, 1-c][1, 4]oxazin-1-oneand its 7-Acyl Derivatives

Starting from 1H-pyrrole, unreported 3, 4-dihydropyrrolo[2, 1-c][l, 4]oxazin-1-one 4, 7-(4-chlorobenzoyl)-3, 4-dihydropyrrolo[2, 1-c][1, 4]oxazin-1-one 5 and 7-benzoyl-3, 4-dihydro-pyrrolo [2, 1-c][1, 4]oxazin-1-one 9 were designed and synthesized. They may have antipyretic and analgesic activities.