Synthesis, Structure Characterization, and Cu^2＋ Recognition of 3-{ [3- （Phenylsulfonamido） benzoyl ] methylidene } -3,4- dihydroquinoxaline-2 （1H） -one

IntroductionSubstituted diketo acid derivatives possess a varie-ty of biological properties, such as analgesic[1—3], anti-bacterial[4]as well as anti-inflammatory[3]. Very re-cently, the results of random screening of millions ofcompounds have shown that…     

Synthesis of （3aS,6aR）- 1,3-Dibenzyl-tetrahydro- 1H-thieno[3,4-d]-imidazole-2（3H）-one-4-ylidenepentanoic Acid and Characterization of Its Crystal

1 INTRODUCTION The title compound, (3aS,6aR)-1.3-dibenzyl- tetrahydro-1H-thieno[3,4-d]-imidazole-2(3H)-one- 4-ylidenepentanoic acid 3, is a key intermediate for the synthesis of d-biotin 1 (VITH, Fig. 1) which has been widely used not only as a pharmaceu…     

Synthesis and Crystal Structure of 1,7,7-Trimethyl- 4-（4-methoxyphenyl）-4,6,7,8-tetrahydroquinoline- 2,5（1H,3H）-diones under Microwave Irradiation

1 INTRODUCTION Various quinolone derivatives are known to dis- play interesting biological properties ranging from microbial activity to cytotoxicity[1]. They have been reported as antiviral (HIV-1)[2] and antitumor agents[3] as well as used as tubulin[4], topoisomerase[5] and thrombocyte inhibitors[6]. As a member of the quino- lone family, substituted N-phenyl-2-quinolones re-present the structural basis of many biologically active compounds, such as protein kinase inhibitors, immunodu…     

Synthesis and Crystal Structure of 7,7- Dimethyl-2-amino-3-cyano-4-(3,4-methylenedioxylphenyl)- 5-oxo-5,6,7,8-tetrahydro-4H-benzo-[b]-pyran

1 INTRODUCTION Inorganic solid supports as catalysts resulting in higher selectivity, milder conditions and easier work-up has been reported as useful catalysts for many reactions [1~3]. Recently, we have reported the Knoevenagel condensation and some other reactions[4~6] catalyzed by KF-Al2O3. In this paper, we discussed the crystal structure of the title compound synthesized by the reaction of 2-cyano-3-(3,4-methylenedioxylphenyl)acrylonitrile and 5,5-dimethyl-1,3-cyclohexanedione in…     

C–H Arylation using acyl thiourea ligands: Applications in the synthesis of 3,6-diaryl-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles

Synthesis of a series of new 3,6-diaryl-[1,2,4]triazolo[3,4-b] [1,3,4]thiadiazoles(5a–o) was achieved by phophine free, C–H arylative cross-coupling of 6-aryl-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles(4a–o)with suitably substituted iodoanilines using 1-(2-naphthoyl)-3-(4-bromophenyl)thiourea as a ligand.The requisite triazolothiadiazoles(4a–o) were obtained by the condensation of 4-amino-1,2,4-triazole-3-thiol(3) with suitably substituted aromatic acids in the presence of phosphoryl chloride.     

Chemoselective Dehydrogenation of 3-[2-（3,4-Dihydro-1-naphthalenyl）ethyl]imidazolidine-2,4-diones： a New and Convenient Synthesis of 13,16-Diazaequilenin analogs

The synthesis of the title compounds starting with the chemoselective dehydrogenation of 3-[2-(3,4-dihydro-1-naphthalenyl)ethyl]imidazolidine-2,4-diones has been described.     

Bischler-Napieralski Reaction of 2-（3, 4-Dimethoxy-2-nitrophenyl）-N- [2-（3, 4-dimethoxyphenyl） ethyl]-N- [（S）-l-phenylethyl] acetamide Accompanied by Elimination of Chiral Auxiliary

Unexpected dealkylation of Bischler-Napieralski cyclization of 2-(3,4-dimethoxy-2-nitro-phenyl)-N-[2-(3,4-dimethoxyphenyl) ethyl]-N-[(S)-1-phenyl-ethyl] acetamide 3 was reported.The electronic effect of the substituent at 2-position of C ring was also discussed.     

Syntheses and Crystal Structures of 4-Amino-3- （3-hyd roxyp ropyl）- 1H-1,2,4-triazole-5（4H）-thione and 6-（4-Biphenylyl）-3-（3-hydroxypropyl）-7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazine

1INTRODUCTION It has been reported that3,6-disubstituted-7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazines have a broad spec-trum of bioactivities,such as antimicrobial[1],antibac-terial,antifungal[2],anti-inflammatory[3],diuretic[4],an-thelmintic and analgesic[5].They can also be used as plant-growth regulating agents[6],photographic coup-lers,dyes for improved preservability and absorption characteristics,and inhibitors of malignant cellularZOU K.H.et al.:Syntheses and Crystal Structures o…     

Synthesis under Microwave Irradiation and Crystal Structure of 4-（3,4-Methylenedioxylphenyl）-6-methyl- 5-ethoxycaronyl-3,4-dihydropyrimidin-2（H）-one

1 INTRODUCTION Since Biginelli firstly reported the synthesis of 3,4-dihydropyrimidin-2(1H)-ones in 1893, this com- pound has been found to emerge as calcium channel blockers, antihypersive agents and a-antagonists[1]. Consequently, this Biginelli reacti…     

Differentiation of Constitutional Isomer of 2,2a,3,4-Tetrahydro- 4-methyl-2a-phenyl-2- （thiophen-2-yl）- 1H-azeto [-2,1-d] [- 1,51benzothiazepin-1-one-5-oxide and Fragmentations of 2,3-Dihydro-2,4-diphenyl-1,5-benzothiazepine-l-oxide／- 1,1-d

Mass spectrometric behaviour of 2,2a, 3,4-tetrahydro-4-methyl-2a-phenyl-2- (thiophen-2-yl)- 1H-azeto [-2,1-d-J1-1,5-]benzothiazepin-l-one-5-oxide and 2,3-dihydro-2,4-diphenyl-1,5-benzothiazepine-l-oxide/-1,1-dioxide have been studied with the aid of mass-analyzed ion kinetic energy spectrometry and accurate mass measurements under electron impact ionization. The monooxide derivatives showed a tendency to eliminate an alkene or an oxygen atom. 1H-Azeto[-2,1-d][1,5]benzothiazepin-1-one-5-oxide could also eliminate the thiophen- 2-ylketene molecule via a reverse [-2 q- 2 ~ cycloaddition. 2,3-Dihydro-2,4-diphenyl- 1,5-benzothiazepine-1-oxide/-1, 1-dioxide could eliminate SO2 or SO, respectively. The structure of 2,2a, 3, 4-tetrahydro-4-methyl-2a-phenyl-2- (thiophen-2-yl)-1H-azeto 1-2,1-d-] [1,5 -] benzothiazepin-1-one-5-oxide was identified on the basis of its fragmentation. The identification was supported by the fragmentations of model compound, 2,3-dihydro-2,4-diphenyl-1,5-benzothiazepine-1-oxide/-1,1-dioxide.     

含吡唑1,2,4-三唑噻二嗪衍生物的合成及抑菌活性

1-苯基-3-甲基-5-氯-4-吡唑甲醛与4-氨基-5-取代苯基-1,2,4-三唑-3-硫酮缩合生成4-(1-苯基-3-甲基-5-氯吡唑次甲亚胺基)-5-(取代苯基)-2H-1,2,4-三唑-3(4H)-硫酮,再烷基加成化为新型含吡唑基5,6-2H-1,2,4-三唑[3,4-b][1,3,4]噻二嗪衍生物。 化合物结构经¹H NMR、IR以及元素分析确认。 初步生物活性测试结果表明,在100 mg/L浓度下,化合物8a(3-(2-甲基苯基)-6-(5-氯-2-甲基-4-苯基吡唑)-7-(4-硝基苯基)-5H-1,2,4-三唑[3,4-b][1,3,4]噻二嗪)对黄瓜炭疽病的抑制率达90%。     

Stereospecific synthesis of 6,7-dihydro-5H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazines

The reaction of 3-mercapto-4-arylideneamino-1,2,4-triazoles 2b-d , 3a-d with ethyl bromoacetate and/or phenacyl bromide in hot DMF and triethylamine affords the stereochemically pure 7-acyl-6-aryl-6,7-dihydro-5H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazines 4b-d , 5a-d , 6b , d in which the consecutive hydrogen atoms N(5)H-C(6)H-C(7)H are cis to each other. This stereochemistry was determined by ¹H NMR spectroscopy and confirmed by comparison with the spectrum of 3,6-diphenyl-6,7-dihydro-5H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazine 10 . The latter was prepared by NaBH₄ reduction of 3,6-diphenyl-5H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazine 9 . The reported reactions offer two interesting stereospecific syntheses of the condensed heterocyclic compounds.     

Synthesis and Crystal Structure of 3,6-Bis（4-methyl-1,2,3-thiadiazol-5-yl）-1,2,4-triazolo[3,4-b][1,3,4]thiadiazole

The compound 3,6-bis(4-methyl-1,2,3-thiadiazol-5-yl)-1,2,4-triazolo[3,4-b][1,3,4] thiadiazole(C9H6N8S3,Mr = 322.40) has been synthesized by the reaction of 4-amino-3-(4-methyl-1,2,3-thiadiazolyl)-5-mercapto-1,2,4-triazole with 4-methyl-1,2,3-thiadiazol-5-carboxylic acid and phosphorus oxychloride,and its structure was characterized by IR,1H NMR,EI-MS,elemental analysis and single-crystal X-ray diffraction.The crystal of the title compound belongs to monoclinic,space group C2/c with a = 2.0053(4),b = 1.3081(3),c = 1.0556(2) nm,β = 112.69(3)°,Z = 4,V = 2.5548(9) nm3,Dc = 1.676 g/cm3,μ = 0.582 mm-1,F(000) = 1312,R = 0.0546 and wR = 0.1523.X-ray analysis indicates that all rings are essentially planar in this molecule,and an intermolecular hydrogen bond C(9)-H(9)…N(2) and weak intramolecular interactions between S(1)…N(7),S(3)…N(1) and S(2)…N(4) are observed.     

6-取代苄硫基-3-(3,4,5-三甲氧基苯基)-1,2,4-三唑[3,4-b][1,3,4]噻二唑类化合物的合成与抑菌活性

以4-氨基-5-(3,4,5-三甲氧基苯基)-3-巯基-1,2,4-三唑为原料,环化得到6-巯基-3-(3,4,5-三甲氧基苯基)-1,2,4-三唑[3,4-b][1,3,4]噻二唑再与取代苄氯反应,得到9个6-取代苄硫基-3-(3,4,5-三甲氧基苯基)-1,2,4-三唑[3,4-b][1,3,4]噻二唑类衍生物3a～3i.其结构经IR,1H NMR,MS和元素分析确证.初步生物活性测试结果表明部分化合物有一定的杀菌活性.     

5,6-2H-1,2,4-三唑[3,4-b][1,3,4]噻二嗪衍生物的合成及抗癌活性测定

取代苯甲醛与4-氨基-5-(3,4,5-三甲氧基苯基)-1,2,4-三唑-3-硫酮(2)缩合生成5-(3,4,5-三甲氧基苯基)-4-取代苯基亚胺基-1,2,4-三唑-3-硫酮(3),再烷基加成化为新型5,6-2H-1,2,4-三唑[3,4-b][1,3,4]噻二嗪衍生物4.化合物结构经1HNMR 13C NMR,IR以及元素分析确认.采用噻唑兰(MTT)比色法进行化合物抑制人体前列腺癌细胞(PC3)体外活性测试,结果表明所合成的化合物具有不同程度的抑制PC3活性,其中化合物4a在10μmol·L-1浓度下对PC3的抑制率为75.9%.     

1H and 13C NMR study of 5-substituted-4- (arylidene)amino-2,4-dihydro-3H-1,2,4-triazole-3-thiones and 6-aryl-3-(D-gluco- pentitol-1-yl)-7H-1,2,4-triazolo[3,4-b] [1,3,4]thiadiazines

Five 5-substituted-4-(arylidene)amino-2,4-dihydro-3H-1, 2,4-triazole-3-thiones (2a-2e) and seven 6-aryl-3-(D-gluco-pentitol-1-yl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazines (3a-3g) were synthesized. The complete 1H and 13C NMR chemical shift assignments were analyzed on one- and two-dimensional NMR techniques, including DEPT, NOE-DIF, COSY, gHMBC, and gHSQC.     

6-取代-3-（3，4，5-三甲氧基苯基）-1，2，4-三唑[3,4-b][1,3,4]噻二唑的合成与生物活性

以3,4,5-三甲氧基苯甲酸为原料,通过4步反应得到4-氨基-5-(3,4,5-三甲氧基苯基)-3-巯基-1,2,4-三唑,再与取代芳酸反应,得到11个6-取代-3-(3,4,5-三甲氧基苯基)-1,2,4-三唑[3,4-b][1,3,4]噻二唑衍生物5a～5k。其结构经IR,1H NMR,MS和元素分析确证。初步生物活性测试结果表明部分化合物有一定的杀菌活性。     

3－苯氧甲基－6－（2，4－二氟苯基）－7H-1,2,4-三唑并[3,4-b][1,3,4]噻二嗪的合成与晶体结构研究

由苯氧乙酸出发，经多步反应，制得3-苯氧甲基－4－氨基－5－巯基－1，2， 4－三唑，它与2-氯－2'，4'－二氟苯乙酮进行环化反应，生成3-苯氧甲基－6－（ 2,4-二氟苯基）－7H-1,2,4-三唑并[3,4-b][1,3,4]噻二嗪，通过元素分析、红外 光谱、核磁共振氢谱与碳谱、质谱进行表征，并利用单晶X射线衍射法测定其结构 。晶体属单斜晶系、P2_(1/c)空间群，a = 1.339(3) nm, b = 1.4683(4) nm, c = 0.8606(2) nm, β = 108.49(2)°, Z = 4, F(000) = 736, R_1 = 0.0509。还 对均三唑并噻二唑两类稠杂环的晶体结构作了比较。     

Synthesis of 3-Alkyl-6-aryl(arylamino)-7H-[1,2,4]triazolo- [3,4-b][1,3,4]thiadiazines

Starting from 5-alkyl-4-amino-4H-1,2,4-triazole-3-thiols and substituted chloroacetanilides, the corresponding (5-alkyl-4-amino-4H-1,2,4-triazol-3-ylsulfanyl)acetanilides were synthesized. The products underwent intramolecular cyclization in boiling phosphoryl chloride to afford 3-alkyl-6-arylamino-7H-[1,2,4]-triazolo[3,4-b][1,3,4]thiadiazines. 3-Alkyl-6-aryl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine hydrobromides were obtained by reaction of 5-alkyl-4-amino-4H-1,2,4-triazole-3-thiols with substituted phenacyl bromides.