KF／Al_2O_3催化下4H－色烯衍生物的合成

水杨醛与氰乙酸酯在KF－Al2O3催化下反应生成4H－色烯的衍生物，产物的结 构通过单晶X射线确证。     

Reaction of 2-cyano[(4-oxo-4H-chromen-3-yl)methylidene]acetohydrazide with phosphorus reagents: Synthesis and evaluation of anticancer activities of some novel 1,2-azaphospholes, 1,2,3-diazaphospholidine,and 1,3,2-diaza-phosphinanes bearing a chromone ring

A series of 1,2-azaphospholes, 1,2,3-diazaphospholidine, 1,3,2-diaza-phosphinanes bearing a chromone ring as well as dialkyl pyrazolopyrimidine phosphonates have been synthesized from treatment of multifunctional 2-cyano[(4-oxo-4H-chromen-3-yl)methylidene]acetohydrazide (2), some phosphorus reagents such as phosphonic acid and its esters, and phosphorus sulfides as well as phosphorus halides in dry dioxane. The isolated products were evaluated for their anticancer activities and on the expression of vascular endothelial growth factor (VEGF) inhibition. Among the isolated products, compounds 3 and 10 exhibited higher effect against breast cancer cells than the reference drug and on the expression of VEGF inhibition.     

Synthesis of novel 1,2,3-thiadizoles and 1,2,3-selenadiazoles as new antimicrobial agents

Abstract

A series of novel 1,2,3-thiadiazoles and 1,2,3-selenadiazoles having a long alkyl chain were synthesized by reacting semicarbazones with SOCl₂ and SeO₂, respectively. The structures of the target compounds 5–12 were confirmed by spectroscopy (IR, ¹H NMR, ¹³C NMR, and MS) and elemental analysis. Their antibacterial and antifungal activities were evaluated against six bacteria (Pseudomonas aeruginosa, Escherichia coli, Klebsiella pneumoniae, Proteus mirabilis, Enterococcus faecalis, Staphylococcus epidermidis, Staphylococcus aureus) and three fungi (Candida albicans, Candida parapsilosis, Candida tropicalis). The results of bioassays indicated that the compounds 5-Dodecyl-4-(4-methoxy-phenyl)-[1-3]selenadiazole (7), 4-Methyl-5-tetradecyl-[1-3]selenadiazole (8) and 5-Dodecyl-4-(4-methoxy-phenyl)-[1-3]thiadiazole (11) displayed moderate antibacterial activity against S. Epidermidis. On the other hand, according to antifungal screening results, compounds 5-Dodecyl-4-phenyl-[1-3]selenadiazole (5), 4-p-Tolyl-5-undecyl-[1-3]selenadiazole (6), and 5-Dodecyl-4-(4-methoxy-phenyl)-[1-3]selenadiazole (7) exhibited significant antifungal activities studied yeast strains.     

甲氧羰基吲哚-3-甲醛苯腙的合成

甲氧羰基吲哚-3-甲醛与苯肼在酸性条件下通过缩合反应合成了4个未见文献报道的新化合物甲氧羰基吲哚-3-甲醛苯腙,其结构经1HNMR,IR和MS确证。     

An Efficient Synthesis of 4,5-Dihydro-3(2H)-pyridazinone Derivatives

Reaction of hydrazine with 5-(2-aryl-2-oxo-ethan-1-yl)-5-R Meldrum's acids 3 gives 4,6-disubstituted 4,5-dihydropyridazin-3(2H)-ones 4 at room temperature. The method is simple and the yield is good. The production of the starting material 3 also is discussed.     

Synthesis of novel 2-phenyl-5-substituted dihydropyrimidines using 2-phenyl-1,3-diaza-1,3-butadienes and electron-deficient olefins

A novel synthetic method for 2,5-disubstituted dihydropyrimidines was developed. The cyclization of 1,3-diaza-4-dimethylamino-1,3-butadienes having a N-protecting group (N-Boc, N-Cbz, N-n-C₄H₉, N-Bn or N-Ph) with electron-deficient olefins, such as α,β-unsaturated carbonyl compounds, phenyl vinyl sulfone, and acrylonitrile was studied in detail. The cyclization smoothly proceeded to afford 4-dimethylamino-1,4,5,6-tetrahydropyrimidines or 1,6-dihydropyrimidines in good yields. The isolated 4-dimethylamino-1,4,5,6-tetrahydropyrimidines were converted to 2,5-disubstituted-1,6-dihydropyrimidines through the β-elimination of the dimethylamino group. 2,5-Disubstituted-1,4(6)-dihydropyrimidines were obtained after removal of the N-Boc or N-Cbz group. Independent tautomers of the resulting dihydropyrimidines were observed.     

2-薁基取代的苯并[b]呋喃类化合物的合成

以溴代丁二酰亚胺为溴化试剂, 对1-氰基-2-甲基薁进行了溴代反应研究, 将溴甲基化产物与水杨醛类衍生物在通常的加热反应及微波辐射条件下进行缩合, 以较高的收率得到2-薁基取代苯并[b]呋喃, 其结构经¹H NMR, IR及元素分析等得以证实.     

Vapor Phase Synthesis of 3-Methylindole over a Ag/SiO2 Catalyst

Ag/SiO₂ was used as an efficient catalyst for the vapor phase synthesis of 3-methylindole from aniline and 1,2-propanediol at atmospheric pressure. When Ag/SiO₂ was calcined at 500 °C for 4 h and the molar ratio of H₂O to H₂ was 0.750 in the reaction, the yield of 3-methylindole could be up to 35%. X-ray diffraction characterization showed that the Ag/SiO₂ catalyst with silver crystallites was active for the synthesis of 3-methylindole.     

Synthesis of 2-methyl-3-nitro-4-phenyl-1,4-dihydroquinoline

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, p. 1696, December, 1989.     

Combining a Click–Multicomponent Reaction: One-Pot Synthesis of 1,2,3-Triazol-4-ylmethyl 3-Amino-5,10-dihydro-5,10-dioxo-1H-pyrazolo[1,2-b]phthalazine-2-carboxylate Derivatives

(1,2,3-Triazol-4-yl)methyl-3-amino-5,10-dihydro-5,10-dioxo-1H-pyrazolo[1,2-b]phthalazine-2-carboxylate derivatives were synthesized by a four-component, one-pot condensation reaction of benzaldehyde derivatives, an active methylene compound (prop-2-ynyl-2-cyanoacetate), azides, and phthalhydrazide in the presence of Cu(OAc)₂/sodium ascorbate as catalysts and 1-methyl-1H-imidazolium trifluoroacetate ([Hmim]TFA) as an ionic liquid medium in good to excellent yields.     

Synthesis and X-ray crystallographic investigation of 3-phenyl-3-phenoxymethyl-2-oxazolidinone

Conclusions 3-Phenyl-5-phenoxymethyl-2-oxazolidinone is the product of interaction of phenylisocyanate with phenylglycidyl ether. Its molecule has a less strained conformation than the molecule of related 2-N-phenylimino-3-phenyl-5-phenoxymethyloxazolidine.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 870–874, April, 1986.     

3-(2-苯并呋喃酰基)薁-1-羧酸甲酯的有效合成

以苯基三甲铵三溴盐(PTAB)为溴化试剂, 对3-乙酰基薁-1-羧酸甲酯进行了溴代反应研究, 将其单溴代产物与水杨醛在温和反应条件下进行缩合, 以极优的收率高选择性得到3-(2-苯并[b]呋喃酰基)薁-1-羧酸甲酯类衍生物, 其结构经¹H NMR, IR及元素分析等得以证实.     

Synthesis and molecular structure oftrans-2-allyl-6-phenyl-1,2,3,6-tetrahydropyridine hydrochloride

When treated with triallylborane and McOH, the product of the 1,2-addition of PhLi to pyridine transforms totrans-2-allyl-6-phenyl-1,2,3,6-tetrahydropyridine. The structure of its hydrochloride was established by X-ray structural analysis.Deceased in 1995.Translated fromIzvestiya Akademii Nauk, Seriya Khimicheskaya, No. 11, pp 2736–2738, November, 1996.     

Synthesis and styrene copolymerization of novel trisubstituted ethylenes: 11. Halogen ring-substituted propyl 2-cyano-3-phenyl-2-propenoates

Abstract

Novel trisubstituted ethylenes, ring-substituted propyl 2-cyano-3-phenyl-2-propenoates, RPhCH=C(CN)CO₂C₃H₇ (where R is 4-chloro-3-fluoro, 2-fluoro-5-iodo, 2-fluoro-6-iodo, 2-trifluoromethyl, 3-trifluoromethyl, 4-trifluoromethyl, 2-trifluoromethoxy, 3-trifluoromethoxy, and 4-trifluoromethoxy) were prepared and copolymerized with styrene. The ethylenes were synthesized by the piperidine catalyzed Knoevenagel condensation of ring-substituted benzaldehydes and propyl cyanoacetate and characterized by CHN analysis, FTIR, ¹H and ¹³C NMR. All the ethylenes were copolymerized with styrene in solution with radical initiation (ABCN) at 70?°C. The composition of the copolymers was calculated from nitrogen analysis, and the structures were analyzed by FTIR, ¹H and ¹³C NMR. Decomposition of the copolymers in nitrogen (TGA) occurred in two steps, first in the 250–500?°C range with residue (0.5–3.1% wt.), which then decomposed in the 500–700?°C range.     

Synthesis and styrene copolymerization of novel trisubstituted ethylenes: 1. Alkyl ring-substituted isopropyl 2-cyano-3-phenyl-2-propenoates

Novel trisubstituted ethylenes, alkyl ring-substituted isopropyl 2-cyano-3-phenyl-2-propenoates, RPhCH = C(CN)CO₂CH(CH₃)₂ (where R is H, 2-methyl, 3-methyl, 4-methyl, 4-ethyl, 4-propyl, 4-i-propyl, 4-butyl, 4-i-butyl, 4-t-butyl) were prepared and copolymerized with styrene. The ethylenes were synthesized by the piperidine catalyzed Knoevenagel condensation of ring-substituted benzaldehydes and isopropyl cyanoacetate, and characterized by CHN analysis, IR, ¹H and ¹³C NMR. All the ethylenes were copolymerized with styrene in solution with radical initiation (ABCN) at 70°C. The compositions of the copolymers were calculated from nitrogen analysis and the structures were analyzed by FTIR, ¹H and ¹³C NMR. Decomposition of the copolymers in nitrogen occurred in two steps, first in the 250–500°C range with residue (2-5% wt.), which then decomposed in the 500–800°C range.     

Reaction of 2-imino-2H-chromene-3-carboxamide with some phosphorus esters: Synthesis of some novel chromenes containing phosphorus heterocycles and phosphonate groups and their antioxidant and cytotoxicity properties

Abstract

Novel chromenyl α-aminophosphonic acid 4 and dialkyl chromenyl phosphonate 6 have been obtained. In addition, some novel types of chromene fused with phosphorus heterocycles such as chromeno[4,3-c][1,2]azaphospholes 5 and 7, chromeno[2,3-d][1,3,2]diazaphosphinine 8 and 1,2-oxaphosphinino[3,4-c]pyridine 10 have been synthesized. The methodology depended on treatment of 2-imino-2H-chromene-3-carboxamide (1) with some phosphorus esters. The synthesized compounds were evaluated for antioxidant and cytotoxic activities. Among the synthesized compounds, compound 5 exhibited the most antioxidant activity with IC₅₀ = 2.8?μg/mL in comparison with ascorbic acid as standard antioxidant. Also, compound 5 had significant cytotoxic effects against four cancer cell lines. Its IC₅₀ values ranged between 4.96 and 7.44?μg/mL in comparison to doxorubicin (IC₅₀ = 0.426–0.493?μg/mL).     

Synthesis of novel 1,2,3-triazole based polycarboxylic acid functionalised ligands for MOF systems

Copper catalysed click reactions are excellent tools to generate various 1,2,3-triazole linked polytopic aromatic carboxylates. The general reaction route involves protection of the carboxylates before proceeding with the click reaction. These polycarboxylate azoles are conveniently prepared for potential utility as novel key building blocks for metal organic frameworks. In one case, the ligand crystallises into a solid structure containing 1D, 2D and 3D features, based on a zigzag 1D structure, a ‘chicken mesh’-like 2D structure and a 3D structure with very well-defined channels.     

Synthesis and characterization of N-3-phenyl-2-propenoyl amino acids

Three N-3-phenyl-2-propenoyl amino acids were synthesized through interaction between 3-phenyl-2-propenoyl chloride and amino acids in alkaline with a high Yield.Structure of the products were identified by elemental analysis,IR and NMR spectroscopy.