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1.
AbstractThis work focuses on optimizing an efficient green synthesis of arylamidoximes from appropriate nitrile and hydroxylamine hydrochloride in water and triethylamine (1.6?mol equivalent) as a base at room temperature for 6?h. This new green synthetic methodology is compared with previously known methods. The main advantages of this new process reported are good yield, easier work-up and short reaction times. Moreover, some of the synthesized arylamidoximes converted to 1,2,4-oxadiazole derivatives 13a,b and 14 via the reaction with (4-acetylphenoxy)acetic acid 12. 相似文献
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Li Fei Nie Khurshed Bozorov Guozheng Huang Jiangyu Zhao Chao Niu 《Phosphorus, sulfur, and silicon and the related elements》2013,188(10):656-667
AbstractHerein, we report the synthesis of 48 novel 3-sulfonylamides containing a tricyclic thieno[2,3-d]pyrimidin-4(3H)-one moiety, and their influence on melanin synthesis in murine B16 cells. All target sulfonylamides were synthesized through key intermediate 3-nitro-thieno[2,3-d]pyrimidin-4(3H)-ones using three types of ipso-nitration reactions. In this case, we converted the pyrido[1,2-a]- fragment of the thieno[2,3-d]pyrimidine moiety to pyrrolo[1,2-a]- and azepino[1,2-a]- side-rings in order to evaluate the bioactivities of the synthesized derivatives for a structure activity-relationships point of view. The obtained results suggest that some of the selected compounds revealed a promising influence on melanin synthesis in murine B16 cells and may serve as lead compounds for further drug discovery and development. 相似文献
4.
Jean-Marie Catel Yves Mollier 《Phosphorus, sulfur, and silicon and the related elements》2013,188(1-2)
Abstract The 3-methylthio-1. 2-dithiolylium including at 5 position a donor substituent, in acetic acid in the presence of pyridine, the 2-methylthio-1. 3-dithiolylium ions in methylene chloride-triethylamine, react with the 2-butene nitrile derivatives and lead to the (A) and (B) corresponding 4-dithiolylidene-2-butene nitriles. In contrast ring opening reaction of the 1, 2-dithiole is observed when 2-cyano-3-phenyl-2-butene nitrile reacts with the 3-methylthio-4-aryl-1. 2-dithiolylium ions in 3 and 5 positions, in methylene chloride-triethylamine. The nucleophilic attack on the 5 position of the dithiolylium ion leads to a 2-cyano-3-phenyl-3 (4-aryl-5-methylthio-2-thienyl) propene nitrile (C), meanwhile the attack on the 3 position leads to a 2-cyano-3-phenyl-3-(4-aryl-3-mercapto-2-thienyl) propene nitrile (D). The proposed structures are established by means of physical methods (IR, NMR, and Mass Spectrometry) and by non ambiguous synthesis. The reactivities of the various sites are explained in function of the electronic and steric effects, furthermore the reaction conditions and the intermediary isolation allow to propose the mecanisms of these reactions. 相似文献
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《Helvetica chimica acta》2017,100(7)
New nitrile‐containing gem‐bisphosphonates as drug candidates for the contrast of osteoporosis are presented, their synthesis being based on the metal catalyzed Michael conjugate addition of trimethylsilyl cyanide to unsaturated bisphosphonate precursors. Zn(OT f)2 turned out to be the most efficient metal catalyst for the reaction enabling the formation of β‐nitrile substituted bisphosphonates in good yields. The corresponding final bisphosphonic acids bearing the nitrile moiety were obtained by deprotection of the ethyl ester moiety. They showed aggregation properties in water due to their amphiphilic nature and will be evaluated in order to assess their biological anti‐osteoclast activity. 相似文献
6.
N. N. Makhova I. V. Ovchinnikov V. G. Dubonos Yu. A. Strelenko L. I. Khmel'nitsky 《Russian Chemical Bulletin》1993,42(1):131-136
A new method of generation of nitrile oxides through interaction of N2O4 with salts of substituted dinitromethanes (1) has been worked out. It has been shown by1H,13C,14N NMR spectroscopy that this reaction proceeds via dinitronitrosomethyl intermediates (one of these has been isolated), and that the reaction is feasible only for substituents capable of conjugation with the nitrile oxide fragment. On the basis of cyclodimerization of the obtained nitrile oxides, preparative methods of synthesis of symmetrically substituted furoxans have been developed.Translated fromIzvestiya Akademii Nauk, Seriya Khimicheskaya, No. 1, pp. 147–151, January, 1993. 相似文献
7.
《合成通讯》2013,43(12):2029-2043
Abstract A novel synthesis of the anti-inflammatory agent 1-(1,2,3,5,6,7- hexahydro-s-indacen-4-yl)-3-[4-(1-hydroxy-1-methyl-ethyl)-furan-2-sulfonyl] urea 1 is described. Sulfonamide 5 was prepared starting from ethyl 3-furoate 2. Key steps were a one-pot sulfonylation with chlorosulfonic acid in methylene chloride followed by pyridinium salt formation and reaction with phosphorus pentachloride to provide ethyl 2-(chlorosulfonyl)-4-furoate 7. This sulfonyl chloride was treated with ammonium bicarbonate to form sulfonamide 8, followed by treatment with excess methyl magnesium chloride to provide 4-(1-hydroxy-1-methyl-ethyl)-furan-2-sulfonamide 5. 4-Isocyanato-1,2,3,5,6,7-hexahydro-s-indacene 16 was prepared from indan in five steps. The formation of the desired sulfonyl urea was carried out both with the isolated isocyanate 16 and via an in situ method. 相似文献
8.
《Green Chemistry Letters and Reviews》2013,6(4):293-300
Abstract 2-Azetidinones possess broad and potent activity due to presence of β-lactam ring and has been established as one of the biologically important scaffolds. The synthesis of N-(4-aryl-2-oxoazetidinone)-isonicotinamide by novel methods of stirring and sonication are described. The conventional method for synthesis of 2-azetidinones involves use of Dean–Stark water separator for the removal of water from the reaction with long reaction time (12–16 h reflux) at a very low temperature (?70 to ?90°C). The microwave method reported requires inert atmosphere of nitrogen gas for the synthesis of 2-azetidinones. We report herein the synthesis of 2-azetidinone analogs of isonicotinic acid hydrazide by novel green route methods of sonication and stirring using molecular sieves. Results indicate that higher yields and shorter reaction times can be achieved by employing novel green route methods of synthesis. 相似文献
9.
Yunpeng Zou Tao Peng Gang Wang Xiaoxue Wen Shuchen Liu Yunbo Sun 《Journal of carbohydrate chemistry》2013,32(9):461-470
AbstractGiven that C-glucosylisoflavones often possess promising biological activities, the development of an efficient synthetic method for this type of molecules is useful for drug discovery. Accordingly, a highly efficient five-step strategy was developed for the total synthesis of puerarin, an isoflavone C-glycoside. An alkyl substituent 4-CH3OC6H4CH2CH2 with an electron-donating group on the aromatic ring was used to enhance the reactivity of phenol and the regioselectivity of O-C rearrangement of phenol glycoside. Thus, coupling of the ethylbenzene derivative of a phenol 1c with glycosyl trifluoroacetimidate 2 resulted in C-glycoside 3c in a 46.2% yield, which was easily de-tert-butylated with trifluoroacetic acid and oxidized with 2,3-dicyano-5,6-dichlorobenzoquinone to produce deoxybenzoin 5. The ring closure reaction of 5 followed by deprotection gave puerarin. This new synthetic strategy is also suitable for the total synthesis of other C-glucosylisoflavones. 相似文献
10.
Frederic Dujols Michel Mulliez 《Phosphorus, sulfur, and silicon and the related elements》2013,188(1):165-191
Abstract Derivatives of β aminoacids in form of esters 1 or nitrile 4 (table I) undergo in an alcohol-ate/alcohol medium a rearrangement (Fig. 2), with formation of a β peptide link, resulting in the formation of esters 6 (table II). According to the experimental conditions the six membered ring heterocycles 5 are detected or isolated. They are also synthetized by cyclisation of acids 2 or hydrazide 3 (Fig. 5). While phosphorus easily reacts with alcohols and water, leading respectively to esters 6 and acids 9 (Fig. 7), it remains unaffected by amines. These results are discussed in term of mechanisms of the phosphorylation. The applications for β peptide synthesis and the participation of the p amide group in phosphorylation are limited. 相似文献
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R. M. Shaker A. F. Mahmoud F. F. Abdel-latif 《Phosphorus, sulfur, and silicon and the related elements》2013,188(1):207-222
Abstract The synthesis and structural characterization of 2-thioxopyrido[2,3-d]pynmidinethiones 5,9,12 and 4,4′-(1,4-phenylene)-di-(2-thioxo-1,2,3,4-tetrahydropyrimidines) 16-22 are described. 相似文献
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A convenient synthesis of 3-substituted pyrazole derivatives by a mixed anhydride method using i-butylchloroformate and N-methylmorpholine at ?20 °C in tetrahydrofuran and study of in vitro antibacterial activities of the prepared compounds against Staphylococcus epidermidis, Bacillus subtilis, Pseudomonas aeruginosa, and Proteus valguris by agar-diffusion method were carried out. The results suggested that the products 4a, 4b, and 4c exhibited moderate to feeble inhibition against all test bacteria at greater concentration but 4d was best against Staphylococcus epidermidis (22 mm) and worst against Pseudomonas aeruginosa (16 mm) at the greatest concentration (2.5 mg/ml), and the activities decreased with decrease in concentration. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resource(s): Full experimental and spectral details.] 相似文献
13.
Mohammed A. Assiri Mamdouh M. Ali I. S. Yahia 《Phosphorus, sulfur, and silicon and the related elements》2013,188(10):668-674
AbstractThe synthesis of some novel chromonyl and pyrazolyl α-aminophosphonates containing a quinazolinone ring was carried out by applying Pudovik and Kabachnik-Fields reactions under solvent- and catalyst-free conditions. The anticancer activities of these compounds were evaluated against five cancer cell lines. 3-{[(3-Phenyl/1,3-diphenyl-1H-pyrazol-4-yl)methylidene]amino}-2-phenyl-quinazolin-4(3H)-ones (3d,e) and diethyl {[3-phenyl/1,3-diphenyl-1H-pyrazol-4-yl][(4-oxo-2-phenyl-quinazolin-3(4H) yl)amino] methyl}phosphonates (4d,e) displayed the potent anticancer activities against HCT116, MCF-7 and HepG2 cell lines in comparison with the standard drug. 相似文献
14.
AbstractA stereoselective total synthesis of 16-membered C2-symmetric macrodiolide Pyrenophorol, Tetrahydropyrenophorol and 4,4-diacetylpyrenophorol have been accomplished. The synthesis started from commercially available L-Aspartic acid and the key reactions involved are regioselective epoxide opening, CBS reduction, Pinnick oxidation and Mitsunobu dilactonization. 相似文献
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Cis 2,6-Diphenyltetrahydrothiapyranone (1) was subjected to Wittig reaction to generate exocyclic double bond (2a-c). Cycloaddition of nitrile oxides and nitrile imines to the latter led to a novel spiro tetrahydrothiapyranoisoxazolines (3a-f) and spiro tetrahydrothiapyranopyrazolines (4a-f) 相似文献
16.
(-)-Drimenol (5) was used as starting material for the synthesis of diastereoisomeric diols 3 and 4, through the nitrile 7, Compounds 3 and 4 are the direct precursors of Ambrox® (1) and 9-epiambrox (2). 相似文献
17.
Alexander I. Kurdjukov Valeriy A. Pavlov 《Phosphorus, sulfur, and silicon and the related elements》2013,188(1-4)
Abstract Ab initio (4–31G?) and semiempirical (MNDO, AMI) quantum-chemical calculations of phosphorus-functionalized and non- phosphorylated nitrile oxides have been done. In approximation of general multielectronic perturbation theory, all nitrile oxides, including trifluoroacetonitrile oxide and dialkoxyphosphorylnitrile oxides, by type of orbital interactions qualify as electron-donor dipoles. 相似文献
18.
《Journal of carbohydrate chemistry》2013,32(6-7):353-374
Abstract Glycosyl nitrile oxides, generated in situ by reaction of glycosyl oximes (3a, 3b, 4) with N‐chlorosuccinimide and DBU, on 1,3‐dipolar cycloaddition with substituted alkenes resulted in glycosyl isoxazolines (5, 7–28) in diastereoselective manner. The extent of diastereoselection varies with the nature of substituents both in sugar and alkenes. The compounds synthesized were screened in vitro against many fungi wherein two of the compounds (12, 23) showed significant inhibition against Sporothrix schenckii, Trychophyton mentagrophytes, and Cryptococcus neoformans with MIC of 12.5 and 6.25 µg/mL, respectively. 相似文献
19.
E. Kh. Ahmed M. A. Ameen F. F. Abdel-latif 《Phosphorus, sulfur, and silicon and the related elements》2013,188(3):497-510
A highly efficient and versatile synthetic approach to the synthesis of pyrido[4′, 3′: 4]thieno[2,3-d]pyrimidines (4, 14, 15, 21) and their heterofused (e.g., triazolo-, triazino-, imidazo-, and tetrazolo-,) pyridothienopyrimidines (5–9, 16, 17, 22–24) is described utilizing 2-amino-3-cyano-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-6-carboxylic acid ethyl ester ( 2 ) and diethyl 2-isothio-cyanate-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3,6-dicarboxylate ( 10 ) as starting materials. 相似文献