Multicomponent Reaction for Synthesis of 2-(Indol-3-yl)pyridine Derivatives Under Microwave Irradiation

A short, practical, and efficient preparation of 2-(indol-3-yl)pyridine derivatives via a one-pot procedure of 3-cyanoacetylindole, chalcones, and ammonium acetate under microwave irradiation was described. All these compounds were obtained in good yield, and their structures were confirmed by ¹H NMR, infrared, and elementary analysis.      

微波辐射下2,7,7-三甲基-3-乙氧羰基-4-(3-硝基苯基) -5-氧代-1,4,5,6,7,8-六氢喹啉的合成和晶体结构

标题化合物C21H24N2O5是由间硝基苯甲醛、达咪酮、乙酰乙酸乙酯、醋酸铵在微波辐射下干反应而得。结构通过单晶X-射线衍射法确定,其晶体属斜方晶系,空间群 Pbcn, a =17.953(3), b =15.206(4), c =14.299(3), V =3904.(2)3, Mr =384.42, Z =8, Dc =1.308g/cm3 , m(MoKa) =0.094mm-1, F(000)=1632。晶体结构用直接法解出,经全矩阵最小二乘法对原子参数进行修正,最终的偏离因子为R=0.0493, wR=0.1078。X-射线分析结果表明,吡啶环为船式构象,与之稠合的六元环为信封式构象。     

Synthesis and Crystal Structure of 1-Phenyl-3-methyl-4-（4-bromophenyl）-6-（2-chlorophenyl）-pyrazolo[3,4-b] Pyridine under Microwave Irradiation

1INTRODUCTIONThepyrazolo[3,4-b]pyridineclassofcompoundspossessmanybiologicalandpharmacologicalactivi-ties[1],suchasactiveanti-concretionmedicaments[2]aswellasactiveanti-gramnegativeandpositivebacteriaagents[3].Thereforethesynthesesofsuchcompoundshavearousedgreatattentionofalargenumberofchemists.Themostimportantsyntheticrouteisthecondensationreaction[4～11]ofamino-pyrazoleandα,β-unsaturatedcompounds.Theorganicreactionundermicrowaveirradia-tionhastheadvantagesoffastreactionspeed,shorttime…     

2,2-二(对烃氧基苯基)丙烷的微波催化合成

在KOH固体碱存在下,利用微波辐射,双酚A与长链卤代烃进行双烃基化反应,以40%~90%的产率生成2,2-二(对烃氧基苯基)丙烷.     

微波作用下3-取代-(1H)-嘧啶［1，2-a］喹啉-1-酮的一步合成法

5-(双甲硫基亚甲基 ) -2 ,2 -二甲基 -1 ,3 -二环己 -1 ,4-二酮 (1 ) [1] 既具有丙二酸亚异丙酯的环状结构 ,又具有乙烯基硫代缩酮的结构特征 .它是一种多功能的合成试剂 ,其最重要性质是可与多种亲核试剂发生加成反应 ,继而消除甲硫基 ,从而可以转变成一系列有用的合成中间体 (2 ) [2～ 5] .若亲核试剂具有两个亲核部位 Nu1及 Nu2 ,则 Nu1反应后 ,Nu2可进一步与丙二酸亚异丙酯的羰基进行分子内的亲核加成 ,从而形成环状化合物 (3 ) ,这一模式已在多种杂环化合物合成中获得应用[6～ 8] .Me SMe SOOMe OOMe　+ Nu1-Nu Me SNu1Nu …     

微波辐射下4-(2-氯苯基)-6-甲基-5-乙氧羰基-3,4-二氢嘧啶-2(H)-酮的合成和晶体结构

标题化合物C14H15ClN2O3是由2-氯苯甲醛、乙酰乙酸乙酯、尿素在TsOH作用下用微波辐射反应得到, 结构通过单晶X-射线衍射法确定, 其晶体属三斜晶系, 空间群P, Mr = 294.73, a = 7.688(1), b = 9.106 (2), c = 11.412(2) ? = 102.963(3), = 105.957(2), g = 102.484(2), V = 714.9(2) ?, Z = 2, Dc = 1.369 g/cm3, = 0.276 mm-1, F(000) = 308, 最终的偏离因子为R = 0.0845, wR = 0.2092。在分子结构中嘧啶环为船式结构, 平面1(苯环)与平面2 ((C(8)C(9) C(10)N(2))之间的两面角为 91.57啊?     

无催化剂条件下微波辐射一步法合成2-氨基-4-芳基-5-氧代-5,6,7,8-四氢-4H-苯并吡喃-3-腈

以芳醛、丙二腈、1,3-环己二酮为原料在无催化剂条件下,分别用微波辐射和传统加热法合成了一系列2-氨基-4-芳基-5-氧代-5,6,7,8-四氢-4H-苯并吡喃-3-腈(4a～4g)衍生物.与常规加热方法相比,微波辐射法具有反应时间短、产率高、后处理方便、环境友好等优点,所有化合物均经IR,1H MMR和元素分析确定.     

Synthesis and Analgesic Activities of Some 2-(Benzazolylacetyl)amino-3-ethoxycarbonylthiophene Derivatives

In this study, some 2-[2-(benzazole-2-thioxy)acetylamino]-3-ethoxycarbonylthiophene and 2-[2-(benzazole-1-yl)acetylamino]-3-ethoxycarbonylthiophene compounds were obtained by the reaction of 2-chloroacetylamino-3-ethoxycarbonylthiophene derivatives and a suitable benzazole-2-thione or benzimidazole derivatives. Analgesic activities of the compounds were tested by using tail-flick and tail-immersion methods. It is reported that some of the compounds showed remarkable analgesic activities.     

微波辐射下一锅法合成2-氨基-6-溴-4-芳基-5H-茚并[1,2-b]吡啶-3-腈衍生物

以芳香醛、4-溴茚酮、丙二腈和醋酸铵为原料,分别用微波辐射和传统加热法,一步法合成7种未见文献报道的2-氨基-6-溴基-4-芳基-5H-茚并[1,2-b]吡啶-3-腈衍生物.对比两种方法,在常压下微波具有反应时间短、产率较高等特点.所有化合物均经IR,1HNMR和元素分析确定.     

微波辐射下合成2-芳甲酰氨基-5-(2-三氟甲基苯并咪唑-1- 亚甲基)-1,3,4-噻二唑

微波辐射下, 1-肼羰亚甲基-2-三氟甲基苯并咪唑与芳酰基异硫氰酸酯反应合成了1-(2-三氟甲基苯并咪唑-1-乙酰基)-4-芳酰基氨基硫脲(1a～1j), 继而在乙酸中合环得到了一系列的2-芳甲酰氨基-5-(2-三氟甲基苯并咪唑-1-亚甲基)-1,3,4-噻二唑(2a～2j), 反应时间短, 产率高, 副反应少. 标题化合物经元素分析, IR, 1H NMR确证结构.     

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…     

2-烷氧基-3H-喹唑啉-4-酮的合成与杀菌活性

研究了合成2-烷氧基-3H-喹唑啉-4-酮衍生物4的方法,该方法应用膦亚胺1与芳基异氰酸酯的氮杂Wittig反应,得到的碳二亚胺2再与醇在醇钠催化下反应,合成了12种未见文献报道的喹唑啉酮衍生物4.所得产物4的结构由NMR,MS,IR所确证.探讨了成环反应的条件以及所合成的新型杂环化合物的杀菌活性,结果表明部分化合物表现出较好的抑菌活性,如41在50 mg/L浓度时,对水稻纹枯菌的抑制率为89%.     

6-氟-4-(N-芳基)胺基喹唑啉类化合物的微波合成及生物活性研究

经2-氨基-5-氟苯甲酸与甲酰胺闭环、氯化反应, 合成了6-氟-4-氯喹唑啉, 然后在微波辐射下与芳香胺反应, 合成了6个新的6-氟-4-(N-芳基)胺基喹唑啉类化合物. 新化合物经¹H NMR, IR及元素分析证明其结构. 体外抑瘤试验证明化合物对前列腺癌细胞(PC3)、人胃癌细胞(BGC823)、人乳腺癌细胞(BCap-37)均无抑制活性. 经ERK的抗磷酸化活性免疫印迹试验证明化合物对小鼠成纤维细胞(NIH3T3)无抑制活性.     

微波促进下无溶剂一锅法合成含氟喹唑啉-4(3H)-酮类化合物

采用邻胺基苯甲酸、原甲酸三乙酯及含氟苯胺为原料,在微波促进下,无溶剂一锅法高效合成了系列3-氟苯基-喹唑啉-4(3H)-酮类化合物,同时测试了新化合物的荧光性能,并与不含氟同类化合物的荧光发射光谱进行了比较.     

二[4-羟基-5,6-二氢-6-烷基(芳基)-2H-吡喃-2-酮-3-]烃的合成及生物活性的研究

采用5,6-二氢-6-烷基(芳基)-2H-吡喃-2,4-二酮和醛进行缩合反应,合成了二[4-羟基-5,6-二氢-6-烷基(芳基)-2H-吡喃-2-酮-3-]烃.其结构经¹HNMR和元素分析证实.对反应条件(反应温度、反应时间)进行了探讨.生物活性初步测定表明,该类化合物具有一定的杀菌和抗烟草花叶病毒的活性.     

HTIB-Mediated One-Pot Synthesis of Some 2-Substituted 4-Styrylthiazoles from (E)-4-Arylbut-3-en-2-ones

The reaction of (E)-4-arylbut-3-en-2-ones with [(hydroxy(tosyloxy)iodo]benzene (HTIB) followed by treatment with thioureas, thioamide, and thiobenzamide has offered a one-pot synthesis of 2-substituted 4-styrylthiazoles.

Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications® to view the free supplemental file.     

1,2,4-Triazines in Organic Synthesis. 9. Synthesis of 3-(3-Ethylindol-2-yl)-5,6,7,8-tetrahydroisoquinoline Using the Fischer Reaction under the Usual Conditions and with Microwave Irradiation

The nucleophilic substitution of hydrogen in 3-methylthio-1,2,4-triazine by the carbanions of nitrobutane and 4-nitrobut-1-ene gave oximes, the selective fission of which using sodium dithionite gave ketones in the case of compounds with a saturated carbon chain. Ketones in Diels-Alder reaction with 1-pyrrolidinocyclohex-1-ene gave 3-acyl-1-methylthio-5,6,7,8-tetrahydroisoquinolines. Phenylhydrazones of the compounds obtained underwent Fischer reaction under usual conditions and also when using microwave irradiation on a solid support. The final 3-(3-ethylindol-2-yl)-5,6,7,8-tetrahydroisoquinoline was obtained via reductive desulfuration using Raney nickel in ethanol.     

A One-Pot,Solvent-Free,and Catalyst-Free Synthesis of Substituted (E)-1-Phenyl-3-[2-(piperidin-1-yl)quinolin-3-yl]prop-2-en-1-ones Under Microwave Irradiation

Russian Journal of Organic Chemistry - A convenient one-pot, three-component, and solvent-free procedure for the preparation of substituted...     

Novel 4-Aryl-2-amino-6-(naphthalene-1-yl)-3-cyanopyridine Derivates as Potential Organic Fluorescent Materials Prepared Under Microwave Irradiation via Three-Component Domino Reactions

A green and efficient method for direct preparation of 3-cyanopyridine from aromatic aldehydes is reported. A series of novel 4-aryl-2-amino-6-(naphthalene-1-yl)-3-cyanopyridine derivates were successfully prepared by one-pot synthesis of three-component domino reactions including aromatic aldehydes, 1-acetylnaphthalene, and dicyanomethane in the presence of ammonium acetate in a solution of ethanol under microwave irradiation. This synthetic method for these compounds possesses many advantages including greater yield and shorter reaction times compared with traditional methods. The structures of these compounds were confirmed by means of high-resolution mass spectrometry, ¹H NMR, ¹³C NMR, and infrared. Moreover, the results of their fluorescent spectra showed that these compounds have good fluorescence intensity excited by the visible light wavelength of 416 nm.     

Synthesis and Crystal Structure of Ethyl 4-(3,4-Methylenedioxylphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyridine-5-carboxylate under Microwave Irradiation

<正>The crystal structure of the title compound (C16H17NO5) has been determined by single-crystal X-ray diffraction. The crystal is of monoclinic, space group C2/c with a = 18.520(2), b = 7.8910(1), c = 21.728(3) A, β = 104.77(1)°, V= 3070.4(7) A3, Mr= 303.31, Z = 8, Dc= 1.312 g/cm3, λ = 0.71073 A,μ(MoKα) = 0.098 mm-1 and F(000) = 1280. The structure was refined to R = 0.0486 and wR = 0.1287. There exist intermolecular hydrogen bonds in the crystal.