Synthesis of 5-aryl-1-methyl-1,2,3,4-tetrahydrobenzo[<Emphasis Type="Italic">a</Emphasis>]phenanthridines

5-Aryl-1-methyl-1,2,3,4-tetrahydrobenzo[a]phenanthridines were synthesized by cascade heterocyclization of the corresponding substituted benzaldehydes with 2-methylcyclohexanone and naphthalen-2-amine in a polar solvent in the presence of hydrochloric acid.     

铜胺络合物作用下取代2-萘酚的交叉偶合反应

在铜(II)-胺络合物作用下, 取代2-萘酚化合物进行交叉偶合反应, 得到几种结构新颖的取代1,1'-联-2-萘酚化合物, 产率44%～90%. 化合物的结构经过核磁、红外光谱及质谱进行确证.     

2-(取代苯乙烯基)-5-取代苯并噁唑的合成及其光性能的研究

通过2-甲基苯并噁唑或2-甲基-5-叔丁基苯并噁唑在KOH/DMF介质中与苯甲醛或取代苯甲醛反应,合成了22个标题化合物,其中13个未见报道。测定了它们的结构和紫外光谱、荧光光谱、荧光量子产率,并对母体化合物的溶剂效应进行了研究。     

两种新型芴类Schiff碱的合成及其溶剂效应和聚集诱导发光性质

2-氨基-9,9-二甲基芴分别与2-羟基-1-萘甲醛和4-二乙胺基水杨醛经Schiff碱反应合成了两种新型芴类Schiff碱 (4和5),其结构经¹H NMR, ¹³C NMR, ESI-MS和元素分析表征。通过紫外-可见吸收光谱和荧光发射光谱初步研究了4和5的溶剂效应和聚集诱导发光性质。结果表明： 4和5的紫外吸收和荧光光谱受质子性溶剂的影响明显高于非质子性溶剂,同时两者具有良好的聚集诱导发光增强效应。THF-H₂-O体系中含水量分别达到60%和70%时, 4和5的荧光强度最大。     

Study of plant coumarins: XIV. Catalytic amination of 7-hydroxycoumarin derivatives

Catalytic amination of 7-hydroxy-6-cyanocoumarin or 7-hydroxy-6-methoxycarbonylcoumarin triflates with substituted anilines, isoquinolin-5-amine, 1H-pyrazol-3-amine, or amino acids of penicillin series affords the corresponding 7-(N-substituted) aminocoumarins. In the amination of the mentioned triflates and also of peuruthenicine tosilate with 2-(piperidin-1-yl)aniline the catalytic system Pd(OAc)₂-BINAP has been efficient.     

Synthesis of novel pyrimidine derivatives with (pyridin-3-ylmethyl)thio and phenylamino moieties and evaluation of their antifungal activity

A series of novel pyrimidine derivatives with (pyridin-3-ylmethyl)thio and phenylamino moieties were synthesized from ethyl acetoacetate, thiourea, 3-pyridinylmethyl chloride hydrochloride, and substituted anilines by multi-step reactions. The structures of the target compounds were characterized by IR, ¹H NMR, ¹³C NMR and elemental analysis. The in vitro antifungal activities against Botrytis cinerea and Sclerotinia sclerotiorum were evaluated. The result showed that N-phenyl-6-methyl-2- ((pyridin-3-ylmethyl)thio) pyrimidin-4-amine (4a) displayed high inhibition activity against Botrytis cinerea with 87.5%inhibition at 100 µg/mL; 4a, and N-(4-isopropylphenyl)-6-methyl-2-((pyridin-3-ylmethyl)thio)pyrimidin-4-amine (4c), N-(4-methoxyphenyl)-6-methyl-2-((pyridin-3-ylmethyl)thio)pyrimidin-4-amine (4d) and N-(2-hydroxy-5-chloro)-6-methyl-2-((pyridin-3-ylmethyl)thio)pyrimidin- 4-amine (4h) exhibited sufficient activities against Sclerotinia sclerotiorum with 86.6% –93.7% inhibitions at the same concentration.     

8-烷基小檗碱的合成

对比研究了乙醚、二氧六环和四氢呋喃(THF)三种溶剂对8位长链烷基取代小檗碱衍生物中间体合成产率的影响. 以四氢呋喃(THF)为反应溶剂, 8-癸基和8-月桂基盐酸小檗碱的产率是以乙醚为溶剂的4倍以上.     

Reaction of hexahydropyirimidine-2,4,6-trione with naphthalen-2-amine and benzaldehydes

Previously unknown 12-aryl-7,8,9,10,11,12-hexahydrobenzo[f]pyrimido[4,5-b]quinoline-9,11-diones were synthesized by three-component condensation of naphthalen-2-amine with substituted benzaldehydes and barbituric acid through intermediate 5-benzylidenebarbituric acids.     

Synthesis of Surface-active Substituted 3H-Indole Quaternary Ammonium Molecules

Two substituted 3H-indole quaternary ammonium molecules were designed andsynthesized using hexamethylphosphoramide (HMPA) as a solvent. The products were purified and characterized by IR, ^1H NMR, MS and elemental analysis.     

Synthesis and spectral properties of new hetarylazo indole dyes

A series of new hetarylazo indole dyes were synthesized by azo coupling of 2-phenyl-, 2-methyl-, and 1-methyl-1-phenyl-1H-indole with diazonium salts derived from 5-methylsulfanyl-1H-1,2,4-triazol-3-amine, 1H-1,2,4-triazol-3-amine, 5-methylisoxazol-3-amine, and 5-amino-1,3,4-thiadiazole-2-thiol. The dyes were characterized by the IR spectra, electronic absorption spectra in the UV and visible regions, and ¹H NMR and mass spectra. The effects of solvent nature, acidity of the medium, temperature, and concentration on the electronic absorption spectra in the visible region and the dependence of the color of the dyes on the nature of heterocyclic fragment were examined. Published in Russian in Zhurnal Organicheskoi Khimii, 2007, Vol. 43, No. 7, pp. 1041–1047. The text was submitted by the authors in English.     

Synthesis and plant-growth regulatory activities of novel imine derivatives containing 1H-1,2,4-triazole and thiazole rings

<正>Eleven new imine derivatives 6 containing 1H-1,2,4-triazole and thiazole rings were synthesized by the condensation of 5-((1H- 1,2,4-triazol-1-yl)methyl)-4-tert-butylthiazol-2-amine with various substituted benzaldehydes.The structures of the title compounds were characterized by ~1H NMR,MS and elemental analysis.The plant-growth regulatory activities of these compounds were evaluated.The primary bioassay results indicated that these target compounds exhibited promising plant-growth regulatory activities.     

Synthesis,Anti-Microbial Activity,and Docking Studies of Novel N-Pyridine Substituted 2-Chlorothieno[2,3-d]pyrimidine Derivatives

Russian Journal of General Chemistry - A series of novel N-pyridine substituted 2-chloro-thieno[2,3-d]pyrimidin-4-amine derivatives has been synthesized and characterized by 1H and 13C NMR...     

Synthesis and Fluorescent Properties of Aminopyridines and the Application in “Click and Probing”

Unsubstituted pyridin-2-amine has a high quantum yield and is a potential scaffold for a fluorescent probe. However, the facile access to conjugated highly substituted aminopyridines and the study of their fluorescent properties is scarce. In this paper, synthesis and fluorescent properties of multisubstituted aminopyridines were studied based on a recently developed Rh-catalyzed coupling of vinyl azide with isonitrile to form a vinyl carbodiimide intermediate, following tandem cyclization with an alkyne. An aminopyridine substituted with an azide group as a potential probe was further designed, synthesized, and evaluated. The “clicking-and-probing” experiment of it on BSA protein showed the potential of aminopyridine as a scaffold of a biological probe.     

4-Azidocinnoline—Cinnoline-4-amine Pair as a New Fluorogenic and Fluorochromic Environment-Sensitive Probe

A new type of fluorogenic and fluorochromic probe based on the reduction of weakly fluorescent 4-azido-6-(4-cyanophenyl)cinnoline to the corresponding fluorescent cinnoline-4-amine was developed. We found that the fluorescence of 6-(4-cyanophenyl)cinnoline-4-amine is strongly affected by the nature of the solvent. The fluorogenic effect for the amine was detected in polar solvents with the strongest fluorescence increase in water. The environment-sensitive fluorogenic properties of cinnoline-4-amine in water were explained as a combination of two types of fluorescence mechanisms: aggregation-induced emission (AIE) and excited state intermolecular proton transfer (ESPT). The suitability of an azide–amine pair as a fluorogenic probe was tested using a HepG2 hepatic cancer cell line with detection by fluorescent microscopy, flow cytometry, and HPLC analysis of cells lysates. The results obtained confirm the possibility of the transformation of the azide to amine in cells and the potential applicability of the discovered fluorogenic and fluorochromic probe for different analytical and biological applications in aqueous medium.     

Synthesis and structure of potential Lewis acid–Lewis base bifunctional catalysts: 1-N,N-dimethylamino-8-borononaphthalene derivatives

A new series of boronate-amine substituted potential bifunctional catalysts have been prepared by directed lithiation of 1-N,N-dimethylnaphthalene, followed by reaction borate esters. Both diisopropyl and pincacol ester derivatives of the resulting boronates were prepared, together with a novel boroxine which shows novel N–B interactions in the crystal structure. The corresponding dimethyl-[8-(difluoroborolyl)-naphthalen-1-yl]-amine was directly accessed from the boroxine by reaction with potassium hydrogen fluoride.     

Novel isocyanide-based three-component synthesis of 3,4-dihydroquinoxalin-2-amine derivatives

Synthesis of a novel class of highly substituted 3,4-dihydroquinoxalin-2-amine derivatives including spirocyclic compounds from three-component condensation reaction of o-phenylenediamines, diverse carbonyl compounds, and isocyanides in the presence of a catalytic amount of p-toluenesulfonic acid in good to excellent yields at room temperature is described.     

Novel stereoselective synthesis of 2,3-dihydro-1H-benzo[f]chromen-3-amine derivatives through a one-pot three-component reaction

A short and stereoselective novel synthesis of benzo[f]chromen-3-amine derivatives in good yields, through a three-component aromatic Betti type reaction under solvent free conditions is reported. The spontaneous reaction occurs in the absence of acid catalysts. The use of chiral 1-phenylethylamine or α,β-unsaturated aldehydes allowed us to prepare enantiopure benzo[f]chromen-3-amine derivatives with good stereoselectivity. Conformational analysis compared with the ¹H NMR data of the products obtained, allowed us to the determine the absolute configuration, which was also confirmed by X-ray analysis.     

Azo coupling of 5-substituted furan-2(3H)-ones and 1H-pyrrol-2(3H)-ones with arene(hetarene)diazonium salts

5-Substituted furan-2(3H)-ones and 1-phenyl-1H-pyrrol-2(3H)-ones reacted with diazonium salts derived from substituted anilines and 1H-1,2,4-triazol-5-amine to give azo coupling products at the methylene group in the heteroring. The products were found to exist as hydrazone tautomers.     

N-Benzyloxycarbonyl-2,2,2-trifluoroacetimidoyl chloride—A convenient reagent for the synthesis of 2-trifluoromethyl-4H-pyrido[1,2-a][1,3,5]triazin-4-one

N-Benzyloxycarbonyl-2,2,2-trifluoroacetimidoyl chloride reacted with pyridin-2-amine derivatives to form substituted 2-trifluoromethyl-4H-pyrido[1,2-a][1,3,5]triazin-4-ones.     

Yb(OTf)3: an efficient catalyst for the synthesis of 3-arylbenzo [f]quinoline-1,2-dicarboxylate derivatives via imino-Diels-Alder reaction

A mild and facile method for the synthesis of 3-arylbenzo[f]quinoline-1,2-dicarboxylate derivatives is reported by an imino-Diels-Alder reaction in high yields (76-92%). This procedure includes a novel three-component reaction of aromatic aldehyde, naphthalen-2-amine, and but-2-ynedioate catalyzed by Yb(OTf)₃ in toluene. The results are obviously different from those of the simple substituted aniline-involved reactions catalyzed by ZnCl₂ or KOH in the literature.